158001-28-6|5-Amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile| Ambeed

Structure of 158001-28-6

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Quality Control of [ 158001-28-6 ] Purity: 97% SDS Specification

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Product Details of [ 158001-28-6 ]

CAS No. :	158001-28-6
Formula :	C₈H₁₂N₄
M.W :	164.21
SMILES Code :	N#CC1=C(N)N(C(C)(C)C)N=C1
MDL No. :	MFCD00128289
InChI Key :	WXEIWFYQLJCWSP-UHFFFAOYSA-N
Pubchem ID :	2797454

Safety of [ 158001-28-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 158001-28-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	5
Fraction Csp3	0.5
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	46.91
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	67.63 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.55
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.05
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.1
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.26
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.83

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.76
Solubility	2.84 mg/ml ; 0.0173 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.06
Solubility	1.43 mg/ml ; 0.00869 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.34
Solubility	7.54 mg/ml ; 0.0459 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.56 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.0

Application In Synthesis of [ 158001-28-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 158001-28-6 ]

[ 158001-28-6 ] Synthesis Path-Downstream 1~35

1
[ 32064-67-8 ]
[ 123-06-8 ]
[ 158001-28-6 ]

Yield	Reaction Conditions	Operation in experiment
96.3%	With triethylamine; In ethanol; at 78.0℃; for 3.0h;	At room temperature, t-butylhydrazine 11 (0.72 g, 8.19 mmol) and triethylamine (1.70 mL, 12.29 mmol) were added to a 50 mL round bottom flask containing 20 mL of absolute ethanol.Then, ethoxymethylenemalononitrile 10 (1.00 g, 8.19 mmol) was slowly added dropwise thereto.The reaction mixture was heated at 78 C for 3 hours.The reaction solution was then cooled to room temperature and spin-dried to obtain a viscous orange solid.Water (30 mL) was then added thereto and the reaction was extracted with CH2Cl2 (3 x 60 mL). The combined organic phases were dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure and concentrated. A fast-curing orange-yellow gum was obtained. The residue was separated with 10% EtOAc in hexane (60 mL), and the mixture was sonicated. The resulting crystalline solid was filtered, washed with a large amount of 10% EtOAc in hexane, and dried to give 5-amino-4-cyano-1-t-butyl-1H-pyrazole 1.29 as a light orange crystal, with a yield of 96.3 %.
83%	With triethylamine; In ethanol; at 100.0℃; for 0.5h;Microwave irradiation;	To a mixture of t-butylhydrazine (1.0 g, 8.2 mmol) and triethylamine (1.1 ml, 8.2 mmol) in anhydrous ethanol (20 ml) was added ethoxymethylene malononitrile (7, 1.0 g, 8.2 mmol) slowly in portions. The mixture was heated in a microwave at 100 C for 30 min. and then concentrated via evaporation of the solvent under a reduced pressure. The residue was washed with ether then dried under a reduced pressure. The product was isolated as a yellow solid in 83 % yield (1.1 g, 6.7 mmol). 1H NMR (200 MHz, CDCl3): delta 7.37 (s, 1 H), 4.54 (s, 2 H), 1.58 (s, 9 H); 13C NMR (50 MHz, CDCl3): delta 150.1, 138.3, 114.7, 77.8, 59.9, 28.9; HRMS (CI) calcd for C8H12N4 (M) 164.1062, found 164.1080.
46 g (87%)	With sodium methylate; In ethanol;	(a) 1-tert-Butyl-5-amino-1H-pyrazole-4-carbonitrile To a mixture of tert-butylhydrazine (40 g, 0.32 mol), sodium methoxide (18 g, 0.32 mol) and ethanol 150 ml) was added ethoxymethylene malononitrile (42 g, 0.32 mol). The reaction mixture was heated to reflux for 2 hours and the solvent was removed in vacuo. The residue was extracted with chloroform, washed with water and the organic layer was concentrated in vacuo to afford 46 g (87%) of 1-tert-butyl-5-amino-1H-pyrazole-4-carbonitrile as a semi-solid.

References: [1]Patent: CN110551130,2019,A .Location in patent: Paragraph 0079-0082.
[2]Tetrahedron Letters,2011,vol. 52,p. 5761 - 5763.
[3]Journal of Medicinal Chemistry,1996,vol. 39,p. 1164 - 1171.
[4]Patent: US5294612,1994,A .
[5]Chemistry - A European Journal,2018,vol. 24,p. 15495 - 15501.

2
[ 122-51-0 ]
[ 158001-28-6 ]
1-tert-butyl-4-cyano-5-<(ethoxymethylene)amino>pyrazole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1164 - 1171.

3
[ 33842-02-3 ]
[ 158001-28-6 ]
1-tert-butyl-5-[chloro(dimethylamino)methyleneamino]-4-cyano-1H-pyrazole [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 321 - 332.

4
[ 75318-43-3 ]
[ 158001-28-6 ]
(4-chloro-[1,2,3]dithiazol-5-ylidene)(1-tert-butyl-4-cyanopyrazol-5-yl)amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 449 - 456.

5
[ 158001-28-6 ]
[ 105-53-3 ]
[ 887748-75-6 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 1177 - 1183.

6
[ 7400-27-3 ]
[ 123-06-8 ]
[ 158001-28-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine; In ethanol; water; at 78.0℃; for 3.0h;	Dissolve tert-butylhydrazine hydrochloride (8 g, 64.20 mmol) and triethylamine (6.50 g, 64.20 mmol) in 500 mL of absolute ethanol. Then, 2-ethoxymethylenemalononitrile (7.83 g, 64.20 mmol) was slowly added dropwise to the reaction flask with stirring. It was heated to reflux at 78 C. After about 3 h, the reaction was monitored by TLC (developer: PE / EtOAc = 1: 1). After the reaction solution was cooled to room temperature, the solvent was concentrated under reduced pressure to remove the solvent, and 100 mL of water and CH 2 Cl 2 (300 mL × 3) were added for extraction. The organic phases were combined, dried by adding an appropriate amount of anhydrous sodium sulfate, and concentrated to obtain an orange-yellow viscous solid. The obtained crude product was dissolved in 60 mL of an ethyl acetate-n-hexane (1: 9) mixed solution, sonicated for about 5 min, and allowed to stand. Observed that a large number of crystal forms precipitated, and filtered (washed 3 times with the ethyl acetate-n-hexane mixed solution). Drying gave 10.11 g of 1-tert-butyl-5-amino-1H-pyrazole-4-carbonitrile as an orange solid product, yield: 96%.
96%	With triethylamine; In ethanol; at 78.0℃; for 3.0h;	tert-butylhydrazine hydrochloride (8g, 64.20mmol) and triethylamine (6.50g, 64.20mmol) In 500 mL of absolute ethanol, 2-ethoxymethylenemalononitrile (7.83 g, 64.20 mmol) was slowly added dropwise to the reaction flask with stirring.It was heated to reflux at 78 C. After about 3 h, the reaction was monitored by TLC (developer: PE / EtOAc = 1: 1).After the reaction solution was cooled to room temperature, the solvent was concentrated under reduced pressure to remove the solvent, and 100 mL of water and CH2Cl2(300 mL × 3) were added for extraction. The organic phases were combined, dried by adding an appropriate amount of anhydrous sodium sulfate, and concentrated to obtain an orange-yellow viscous solid.The obtained crude product was dissolved in 60 mL of an ethyl acetate-n-hexane (1: 9) mixed solution, sonicated for about 5 min, and allowed to stand. Observed that a large number of crystal forms precipitated, and filtered (washed 3 times with the ethyl acetate-n-hexane mixed solution) Drying gave 10.11 g of 1-tert-butyl-5-amino-1H-pyrazole-4-carbonitrile as an orange solid product, yield: 96%.
94%		To a suspension of fe/ -butylhydrazine hydrochloride (15.0 g, 120.4 mmol) in ethanol (600 ml_) was added triethylamine (16.8 ml_, 120.4 mmol). The mixture was stirred for 60 min until the hydrazine had dissolved. Ethoxymethylenemalononitrile (14.7 g, 120.4 mmol) was added in portions and the reaction mixture was heated to 80 C and stirred at this temperature overnight. The reaction mixture was concentrated to dryness and the obtained residue was taken up in EtOAc. The organic layer was washed with water, dried over Na2S04, filtered and concentrated under reduced pressure. The solid was then recrystallized in DCM to afford 5-amino-1 -fe/?-butyl-pyrazole-4-carbonitrile (18.6 g, 1 13.4 mmol, 94% yield) as a light yellow solid. LC-MS (ES+, method 1): 1 .36 min, m/z 165.1 [M+H]+

83%	With triethylamine; In ethanol; for 3.0h;Reflux;	In tert-butylhydrazine hydrochloride (8.67 g, 69.6 mmol)Was added triethylamine (9.7 mL, 69.6 mmol)After adding anhydrous ethanol (460 mL), the mixture was stirred and dissolved at room temperature,Ethoxymethylenemalononitrile (8.5 g, 69.6 mmol) was added in small portions.After heating the solution to reflux for 3 hours,After cooling, the solvent was evaporated to give an orange solid.And extracted with ethyl acetate (0.5 L) and water (0.25 L)After drying by adding magnesium sulfate,The organic layer was evaporated to give an orange-yellow solid.The resulting solid was continuously washed with a 10% ethyl acetate in cyclohexane solution to give a crystalline solid5-amino-1-tert-butyl hydrogen - pyrazol-4-cyano 9.54g(Yield: 83%).
83%	With triethylamine; In ethanol; at 20.0℃; for 3.0h;Reflux;	Triethylamine (9.7mL, 69.6mmol) was added to tert-butylhydrazine hydrochloride (8.67g, 69.6mmol) After adding absolute ethanol (460mL) and stirring at room temperature to dissolve, Ethoxymethylenemalononitrile (8.5 g, 69.6 mmol) was added in small portions, the solution was heated to reflux for 3 hours, and then the solvent was evaporated in vacuo to obtain a crude orange product. It was extracted with a mixed solution of ethyl acetate (0.5 L) and water (0.25 L), dried over anhydrous magnesium sulfate, and the organic layer was evaporated to obtain an orange solid. Continue to wash the obtained solid with a cyclohexane solution containing 10% ethyl acetate to obtain crystalline solid 5-amino-1-tert-butyl 1hydro-pyrazole-4-cyano 9.54g (yield 83% ).
64.4%	With triethylamine; In ethanol; for 3.0h;Heating / reflux;	A mixture of t-butylhydrazine hydrochloride (4.67 g, 53 mmol) and triethylamine (5.35 g, 53 mmol) in anhydrous ethanol (250 ml) was stirred and ethoxymethylene malononitrile (6.47 g, 53 mmol) was slowly added in portions. The mixture was heated at reflux for 3 hr. The solvent was removed in vacuo and the product was crystallized from ethyl acetate -hexane followed by ether to afford the title compound as light pale brown crystals (5.6 g, 64.4 %); LC/MS, API-ES, Neg, (M-H)", 163.0.
	With triethylamine; In ethanol; for 3.0h;Heating / reflux;	A mixture of t-butylhydrazine hydrochloride (4.67 g, 53 mmol) and triethylamine (5.35 g, 53 mmol) in anhydrous ethanol (250 ml) was stirred and ethoxymethylene malononitrile (6.47 g, 53 mmol) was slowly added in portions. The mixture was heated at reflux for 3 hr. The solvent was removed in vacuo and the product was crystallized from ethyl acetate - hexane followed by ether to afford 5-amino-l-tert-butyl-lH-pyrazole-4-carbonitrile as light pale brown crystals (5.6 g, 34.1 mmol); LC/MS, API-ES, Neg, (M-H)", 163.0.
	With triethylamine; In ethanol; at 82.0℃; for 3.0h;Inert atmosphere;	[0814] Example 1: 5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile (I1): . In a 250mL flame-dried argon purged round bottom flask, triethylamine (1.78g, 17.7mmol), and t- butyl hydrazine hydrochloride (1.56g, 12.5mmol) are dissolved in anhydrous ethanol (85mL). Ethoxymethylenemalononitrile (1.98g, 17.7mmol) is added slowly and reaction mixture is brought to reflux at 82C for 3 hours. The solvent is removed in vacuo and 10% ethyl acetate / hexane is added (5mL) and the mixture is sonicated (or simply utilize recrystallization from 10% ethyl acetate / hexane). The resulting crystalline solid is filtered, and washed with ether to yield I1. LC-MS (ES+) calcd for C8H12N4 (M+H)+ 165.11, found 165.05.

References: [1]Patent: CN110526921,2019,A .Location in patent: Paragraph 0094-0095; 0098; 0114.
[2]Patent: CN110467618,2019,A .Location in patent: Paragraph 0080; 0090-0092.
[3]MedChemComm,2017,vol. 8,p. 640 - 646.
[4]Patent: WO2017/46604,2017,A1 .Location in patent: Paragraph 00228.
[5]Organic Letters,2012,vol. 14,p. 3906 - 3908.
[6]Patent: CN106008527,2016,A .Location in patent: Paragraph 0048; 0049; 0050; 0051.
[7]Patent: CN110642861,2020,A .Location in patent: Paragraph 0065-0069.
[8]European Journal of Organic Chemistry,2008,p. 3377 - 3381.
[9]Patent: WO2007/126841,2007,A2 .Location in patent: Page/Page column 73.
[10]Patent: WO2009/62118,2009,A2 .Location in patent: Page/Page column 170.
[11]Patent: WO2017/161344,2017,A1 .Location in patent: Paragraph 0813-814.
[12]Journal of Medicinal Chemistry,2017,vol. 60,p. 9976 - 9989.

7
[ 158001-28-6 ]
[ 887748-84-7 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 1177 - 1183.

8
[ 158001-28-6 ]
[ 887748-85-8 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 1177 - 1183.

9
[ 158001-28-6 ]
[ 887748-86-9 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 1177 - 1183.

10
[ 158001-28-6 ]
6-t-butyl-4-oxo-2-(2-furyl)-pyrazolo[3,4-b]imidazolo[4,5-d]pyridine [ No CAS ]

References: [1]Synthetic Communications,2006,vol. 36,p. 1177 - 1183.
[2]Synthetic Communications,2006,vol. 36,p. 1177 - 1183.

11
[ 158001-28-6 ]
4-methoxy-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidine-6-carbonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 449 - 456.

12
[ 158001-28-6 ]
[ 461670-35-9 ]

References: [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 321 - 332.

13
[ 158001-28-6 ]
[ 461670-44-0 ]

References: [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 321 - 332.

14
[ 158001-28-6 ]
[ 461670-46-2 ]

References: [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 321 - 332.

15
[ 158001-28-6 ]
[ 461670-48-4 ]

References: [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 321 - 332.

16
[ 158001-28-6 ]
[ 461670-50-8 ]

References: [1]European Journal of Medicinal Chemistry,2001,vol. 36,p. 321 - 332.

17
[ 158001-28-6 ]
[ 174648-67-0 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1164 - 1171.

18
[ 158001-28-6 ]
[ 174648-59-0 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1164 - 1171.

19
[ 158001-28-6 ]
[ 1027398-48-6 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1164 - 1171.

20
[ 158001-28-6 ]
[ 162401-15-2 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1164 - 1171.

21
[ 77287-34-4 ]
[ 158001-28-6 ]
1-(1,1-dimethylethyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	at 180.0℃; for 5.0h;	In a 100mL round-bottomed flask, add 1-tert-butyl-5-amino-1H-pyrazole-4-carbonitrile (5g, 30.47mmol), 80mL formamide solution, and heat the mixture in an oil bath to 180 C. After about 5 h, the reaction was monitored by TLC (developer: PE / EtOAc = 1: 1). After the reaction solution was cooled, 50 mL of water and CH 2 Cl 2 (200 mL × 3) were added for extraction. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (eluent: PE / EtOAc = 4/1). -1/1) gave the product 1-tert-butyl-4-amino-1H-pyrazolo [3,4-d] pyrimidine as a white solid, 5.82 g, yield: 91%.
91%	at 180.0℃; for 5.0h;	In a 100 mL round bottom flask, add 1-tert-butyl-5-amino-1H-pyridine The azole-4-nitrile (5 g, 30.47 mmol), 80 mL of a formamide solution, the mixture was placed in an oil bath and heated to 180 C., and after about 5 h, the reaction was monitored by TLC (developing solvent: PE / EtOAc = 1: 1).After the reaction solution was cooled, 50 mL of water and CH2Cl2(200 mL × 3) were added for extraction. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (eluent: PE / EtOAc = 4 / 1-1 / 1) 5.82 g of 1-tert-butyl-4-amino-1H-pyrazolo [3,4-d] pyrimidine was obtained as a white solid, yield: 91%.
77%	at 180.0℃; for 0.5h;Microwave irradiation; Inert atmosphere;	A mixture of <strong>[158001-28-6]5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile</strong> (8, 1.1 g, 6.7 mmol) in formamide (15 ml) under a nitrogen atmosphere was heated in a microwave at 180 C for 30 min. The mixture was extracted with EtOAc (3 x 30 ml) and the organic layer was washed successively with sodium carbonate (30 ml), water (30 ml) and brine (30 ml). The organic layer was dried with magnesium sulfate, filtered and concentrated via evaporation of the solvent under a reduced pressure. The product was isolated as a brown solid in 77 % yield (0.97 g, 5.1 mmol). 1H NMR (200 MHz, CDCl3) delta 8.31 (s, 1 H), 7.85 (s, 1 H), 6.17 (s, 2 H), 1.77 (s, 9 H); 13C NMR (50 MHz, CDCl3) delta 157.9, 154.4, 153.2, 128.9, 102.1, 60.4, 29.2; HRMS (CI) calcd for C9H13N5 (M) 191.1171, found 191.1180.

77%	for 6.0h;Reflux;	A solution of 5-amino-1-tert-butyl 1-hydro-pyrazole-4-cyano (8,1.1 g, 1.1 mmol)Was added formamide (15 mL),The mixture was heated under reflux for 6 hours.The mixture was extracted with ethyl acetate (3 x 30 mL)The resulting organic layer was dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure to give a brown solid(0.97 g, 0.97 mmol) (yield 77%).
76%	for 6.0h;Reflux;	To 5-amino-1-tert-butyl-1H-pyrazole-4-cyano (1.1g, 6.75mmol) was added formamide (15mL), heated to reflux for 6 hours to obtain a reaction solution, the reaction solution was treated with ethyl acetate The ester (3×30mL) was extracted, and the resulting organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure to obtain a brown solid (0.97g, 5.1mmol) (yield 76%).
60.9%	at 185.0℃; for 3.0h;	A mixture of S-amino-l-terZ-butyl-lH-pyrazole^-carbonitrile (5.5 g, 33.5 mmol) (Step A) and formamide (68 ml) was heated at 185 C for 3 hr under nitrogen atmosphere. The mixture was added to water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution followed by aqueous wash and brine. The organic layer was dried (anhydrous sodium sulfate) and the <n="75"/>solvent was removed in vacuo to afford a residue which was crystallized from small amount of ether to afford the title compound (3.91 g, 60.9 %); LC/MS, API-ES, Pos, (M+H)+, 192.1.
59%	at 185.0℃;	A solution of 5-amino-1 -fe/?-butyl-pyrazole-4-carbonitrile (18.0 g, 0.1 1 mol) in formamide (131 ml_, 3.29 mol) was stirred at 185 C overnight. Subsequently, the reaction mixture was cooled to room temperature, water was added and the aqueous phase was extracted with EtOAc. The combined organics were washed with sat. NaHC03 solution, dried over Na2S04, filtered and concentrated in vacuo. The obtained crude product was recrystallized in DCM to afford 1 -fe/?-butylpyrazolo[3,4- c ]pyrimidin-4-amine (12.3 g, 64.3 mmol, 59% yield) as a white solid. UPLC-MS (ES+, Short acidic): 1 .04 min, m/z 192.0 [M+H]+
55.8%	at 190.0℃; for 6.0h;Inert atmosphere;	Under nitrogen, <strong>[158001-28-6]5-amino-4-cyano-1-tert-butyl-1H-pyrazole</strong> 12 (1.00 g, 6.09 mm ol)The mixture with formamide (15 ml) was heated at 190 C for 6 hours. The mixture was extracted with CH2Cl2 (3 x 60 ml) and H2O (30 ml). The combined organic layers were then dried over anhydrous sodium sulfate and evaporated in vacuo. The reaction mixture was purified by silica gel column chromatography (elution: 0% to 50% CH2Cl2 / CH3OH) to obtain product 13 as a 1.16 g of a white solid with a yield of 55.8%.
	at 185.0℃; for 3.0h;	A mixture of 5-amino-l-ter?-butyl-lH-pyrazole-4-carbonitrile (5.5 g, 33.5 mmol) (Step A) and formamide (68 ml) was heated at 185 0C for 3 hr under nitrogen atmosphere. The mixture was added to water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution followed by aqueous wash and brine. The organic layer <n="172"/>was dried (anhydrous sodium sulfate) and the solvent was removed in vacuo to afford a residue which was crystallized from small amount of ether to afford l-fert-butyl-lH-pyrazolo[3,4- phiyrimidin-4-ylamine (Compound No. 12; 3.91 g, 20.4 mmol); LC/MS, API-ES5 Pos, (M+H)+, 192.1.
	at 180.0℃; for 4.0h;	Preparation #26. 3-Bromo-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine A suspension of <strong>[158001-28-6]5-amino-1-tert-butyl-1H-pyrazole-4-carbonitrile</strong> (8.67 g, 0.0528 mol) in formamide (100 mL) was heated at 180 C. for about 4 hours. The reaction mixture was cooled, poured into ice water (200 mL), and the product was extracted with ethyl acetate (480 mL). The combined organic layers were dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was taken up in ether (35 mL) and the precipitate was filtered, washed with ether (50 mL), and dried under reduced pressure to afford 1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (3.22 g, 0.0169 mol) as a white solid; RP-HPLC (30% to 95% acetonitrile/0.01M aqueous ammonium acetate, buffered to pH 4.5, over 4.5 min at 0.8 mL/min; lambda=190-700 nm; Genesis C18, 120 A, 3 mum, 304.6 mm column) Rt 1.38 min.
	at 180.0℃; for 3.0h;	[0815] Example 2: 1-(tert-butyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (I2): . Formamide (35mL) is added to intermediate I1 (~2.75g) and the mixture is headed to 180C for 3 hours. Upon cooling, the mixture is added to water and extracted with ethyl acetate using sodium bicarbonate to wash the organic followed by a careful water wash as to avoid emulsion and lastly a wash with saturated brine. The organic layer is dried in vacuo and is recrystallized from a small amount of ether to yield intermediate I2. LC-MS (ES+) calcd for C9H13N5 (M+H)+ 192.12, found 192.21.

References: [1]MedChemComm,2017,vol. 8,p. 640 - 646.
[2]Patent: CN110526921,2019,A .Location in patent: Paragraph 0094-0095; 0098; 0115.
[3]Patent: CN110467618,2019,A .Location in patent: Paragraph 0080; 0090; 0093-0094.
[4]Tetrahedron Letters,2011,vol. 52,p. 5761 - 5763.
[5]Patent: CN106008527,2016,A .Location in patent: Paragraph 0052; 0053; 0054; 0055.
[6]Patent: CN110642861,2020,A .Location in patent: Paragraph 0065; 0070-0073.
[7]Patent: WO2007/126841,2007,A2 .Location in patent: Page/Page column 73-74.
[8]Patent: WO2017/46604,2017,A1 .Location in patent: Paragraph 00229.
[9]Patent: CN110551130,2019,A .Location in patent: Paragraph 0079; 0083-0085.
[10]Patent: WO2009/62118,2009,A2 .Location in patent: Page/Page column 170-171.
[11]Patent: US2006/25383,2006,A1 .Location in patent: Page/Page column 99-100.
[12]Patent: WO2017/161344,2017,A1 .Location in patent: Paragraph 0813; 0815.
[13]Journal of Medicinal Chemistry,2017,vol. 60,p. 9976 - 9989.

22
[ 7722-84-1 ]
[ 158001-28-6 ]
5-amino-1-tert-butyl-1H-pyrazol-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13.2 g (75%)	With potassium hydroxide; In water;	(a) To a mixture of water (500 ml) and 85% KOH (37.91 g) at 0 C. was added 30% H2 O2 (49.4 ml, 483 mmol), followed by 1-tert-butyl-5-amino-1H-pyrazole-4-carbonitrile (15.83 g, 96.5 mmol). The reaction mixture was stirred for four hours at 0 C. and then at room temperature for 1 hour. A yellow precipitate had formed which was collected by filtration and air dried to afford 13.2 g (75%) of 1-tert-butyl-5-amino-1H-pyrazole-4-carboxamide, m.p. 193-195 C.

References: [1]Patent: US5736548,1998,A .

23
[ 158001-28-6 ]
[ 1050619-87-8 ]
[ 1050619-76-5 ]
1-tert-butyl-1H-pyrazole-4-carbonitrile [ No CAS ]

References: [1]European Journal of Organic Chemistry,2008,p. 3377 - 3381.

24
[ 158001-28-6 ]
[ 862728-61-8 ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 5761 - 5763.
[2]Patent: CN106008527,2016,A .
[3]Patent: WO2017/46604,2017,A1 .
[4]MedChemComm,2017,vol. 8,p. 640 - 646.
[5]Patent: WO2017/161344,2017,A1 .
[6]Journal of Medicinal Chemistry,2017,vol. 60,p. 9976 - 9989.
[7]Patent: WO2007/126841,2007,A2 .
[8]Chemistry - A European Journal,2018,vol. 24,p. 15495 - 15501.
[9]Patent: CN110526921,2019,A .
[10]Patent: CN110551130,2019,A .
[11]Patent: CN110642861,2020,A .

25
[ 158001-28-6 ]
1-(t-butyl)-3-(4-methylphenyl)-4-aminopyrazolo[3,4-d]pyrimidine [ No CAS ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 5761 - 5763.

26
[ 158001-28-6 ]
PP₂ [ No CAS ]

References: [1]Tetrahedron Letters,2011,vol. 52,p. 5761 - 5763.

27
[ 158001-28-6 ]
[ 1390635-66-1 ]

References: [1]Organic Letters,2012,vol. 14,p. 3906 - 3908.

Yield	Reaction Conditions	Operation in experiment
83.2%		General procedure: 30 ml of dry ethanol were added to cyclopentylhydrazine hydrochloride (Intermediate P1) (4.660 g, 26.92 mmcl), then (ethoxymethyLene)malononitrile(3.355 g, 26.92 mmol) and triethylamine (11.409 ml, 81.04 mmol) were added. The mixture was heated at ref lux for 3 hours. The crude product was isolated by extraction with ethyl acetate, aqueous layer was washed with water and brine, dried with sodium sulphate and concentrated. Obtained product was purified by chromatography on siLicagel (heptan/ethyl acetate, gradient from 4:1 to 1:1).2.231 g of the title product were obtained as a beige solid (yield 47%). 1H NMR (300 MHz, DMSO-d6): delta 7.52 (s, 1H), 6.52 (s, broad, 2H), 4.55 (q, 1H),1.82 (m, 6H), 1.57 (m, 2H). 13C NMR (75 MHz, DMSO-d6): delta 151.59; 140.51;116.08; 72.86; 57.18; 32.02; 24.78.

29
[ 158001-28-6 ]
4-(4-amino-1-(tert-butyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol [ No CAS ]

References: [1]Patent: CN106008527,2016,A .
[2]Chemistry - A European Journal,2018,vol. 24,p. 15495 - 15501.
[3]Patent: CN110642861,2020,A .

30
[ 158001-28-6 ]
C₃₀H₃₉N₅O₇S [ No CAS ]

References: [1]Patent: CN106008527,2016,A .
[2]Patent: CN110642861,2020,A .

31
[ 158001-28-6 ]
C₂₃H₃₂FN₅O₄ [ No CAS ]

References: [1]Patent: CN106008527,2016,A .

32
[ 158001-28-6 ]
2-(2-(2-(2-(4-(4-amino-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidine-3-yl)phenoxy)ethoxy)ethoxy)ethoxy)ethanol [ No CAS ]

References: [1]Patent: CN106008527,2016,A .

33
[ 158001-28-6 ]
1-tert-butyl-3-[1-(phenylsulfonyl)-1H-indol-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

References: [1]MedChemComm,2017,vol. 8,p. 640 - 646.

34
[ 158001-28-6 ]
1-tert-butyl-3-(1H-indol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

References: [1]MedChemComm,2017,vol. 8,p. 640 - 646.

35
[ 158001-28-6 ]
1-tert-butyl-3-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]

References: [1]MedChemComm,2017,vol. 8,p. 640 - 646.

Historical Records

Technical Information

• Blaise Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Aldehydes and Ketones • Preparation of Amines • Reactions of Amines • Ritter Reaction • Specialized Acylation Reagents-Vilsmeier Reagent • Thorpe-Ziegler Reaction • Ugi Reaction

Related Functional Groups of
[ 158001-28-6 ]

Amines

A112613 [442850-71-7]

1-(tert-Butyl)-1H-pyrazol-5-amine

Similarity: 0.82

A389243 [5334-43-0]

5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

Similarity: 0.78

A270951 [103646-82-8]

5-Amino-1-(p-tolyl)-1H-pyrazole-4-carbonitrile

Similarity: 0.74

A898285 [1124-16-9]

5-Amino-1-isopropyl-3-methylpyrazole

Similarity: 0.73

A158859 [3528-58-3]

1-Ethyl-1H-pyrazol-5-amine

Similarity: 0.73

Nitriles

A222876 [149139-43-5]

1-(tert-Butyl)-1H-pyrazole-4-carbonitrile

Similarity: 0.84

A389243 [5334-43-0]

5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

Similarity: 0.78

A270951 [103646-82-8]

5-Amino-1-(p-tolyl)-1H-pyrazole-4-carbonitrile

Similarity: 0.74

A159852 [64096-91-9]

4H-Benzo[4,5]imidazo[1,2-b]pyrazole-3-carbonitrile

Similarity: 0.73

A152517 [5334-28-1]

5-Amino-1-(4-bromophenyl)-1H-pyrazole-4-carbonitrile

Similarity: 0.69

Related Parent Nucleus of
[ 158001-28-6 ]

Pyrazoles

A222876 [149139-43-5]

1-(tert-Butyl)-1H-pyrazole-4-carbonitrile

Similarity: 0.84

A112613 [442850-71-7]

1-(tert-Butyl)-1H-pyrazol-5-amine

Similarity: 0.82

A389243 [5334-43-0]

5-Amino-1-phenyl-1H-pyrazole-4-carbonitrile

Similarity: 0.78

A270951 [103646-82-8]

5-Amino-1-(p-tolyl)-1H-pyrazole-4-carbonitrile

Similarity: 0.74

A898285 [1124-16-9]

5-Amino-1-isopropyl-3-methylpyrazole

Similarity: 0.73

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CAS No.: 158001-28-6

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