63558-65-6|4-Chloro-5-iodopyrimidine| Ambeed

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Quality Control of [ 63558-65-6 ] Purity: 98% SDS Specification

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Product Details of [ 63558-65-6 ]

CAS No. :	63558-65-6
Formula :	C₄H₂ClIN₂
M.W :	240.43
SMILES Code :	ClC1=NC=NC=C1I
MDL No. :	MFCD08276157
InChI Key :	BIWOQXBVRYUITN-UHFFFAOYSA-N
Pubchem ID :	11230204

Safety of [ 63558-65-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 63558-65-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	39.76
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	25.78 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.67
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	1.81
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.73
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.	1.16
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	2.67
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.81

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.03
Solubility	0.226 mg/ml ; 0.000942 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.97
Solubility	2.57 mg/ml ; 0.0107 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-3.23
Solubility	0.143 mg/ml ; 0.000596 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	Yes
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	Yes
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.	-6.48 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	1.0 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)	1.79

Application In Synthesis of [ 63558-65-6 ]

* 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 [ 63558-65-6 ]

[ 63558-65-6 ] Synthesis Path-Downstream 1~35

1
[ 110-00-9 ]
[ 63558-65-6 ]
[ 63558-78-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1977,p. 621 - 624.

2
[ 188290-36-0 ]
[ 63558-65-6 ]
[ 58758-99-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1977,p. 621 - 624.

3
[ 4349-07-9 ]
[ 63558-65-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With oxalyl dichloride; N,N-dimethyl-formamide; In 1,2-dichloro-ethane; for 3h;Heating / reflux;	To a stirred solution containing 7.7 mL (99 MMOL) of DMF and 150 mL of DICHLOROETHANE at 0C was added 12.7 mL (144.6 MMOL) of OXALYL chloride slowly to control vigorous gas evolution. After the evolution of gas had ceased, 10.0 g of iodopyrimidone was added and the reaction mixture was heated at reflux for 3h, then cooled to room temperature and partitioned between water and DICHLOROMETHANE. The organic layers were dried over MGS04 and the solvent was removed under reduced pressure to give 9.6 g (88%) of the title COMPOUND. 1H-NMR (300 MHz, CDCI3) A 8. 89 (s, 1H) and 8.98 (s, 1H) ; ESIMS : 241.1 (M+H)+
83%	With oxalyl dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; for 2h;Reflux;	Oxalyl chloride (1 .27 ml, 14.61 mmol) was added dropwise in 707 ml dimethylformamide and 20 ml dichloroethane. 5-lodopyrimidin-4(3/-/)-one ( 1 g, 4.55 mmol) was added and the reaction was heated at reflux for 2 h. The reaction mixture was dissolved in dichloromethane, washed with water, dried over sodium sulphate, filtered and concentrated under reduced pressure to give 0.91 g (83 % yield) of the title compound as a solid. Purity 100%.LRMS (m/z): 241 (M+1 )+
75.9%	With oxalyl dichloride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; at 0 - 85℃; for 4h;	N,N-dimethylformamide (3.9 mL, 27.0 mmol) was dissolved in 1,2-dichloroethane (90 mL) at 0 C, the reaction was stirred for 10 min, and oxalyl chloride (6.8 mL, 27.0 mmol) was added dropwise. ),After 20 minutes of dropwise addition, 5-iodopyrimidine-4(3H)one (5.0 g, 22.5 mmol) was added.The temperature was raised to 85 C for 4.0 h, and the reaction solution was concentrated.The residue was dissolved in dichloromethane (120 mL).The organic phase was washed with saturated brine (20 mL×2).Dry anhydrous sodium sulfate (20g),Filter and concentrate to give 4.1 g of a brown oil.The yield was 75.9%. The product was directly subjected to the next reaction without purification.

	With trichlorophosphate; In methanol; water; toluene;	Method V Preparation of 4-Chloro-5-iodopyrimidine 5-Iodo-4(3H)-pyrimidinone (1 eq.) was suspended in toluene to which was added POCl3 (2.0 eq.). The reaction mixture was heated to reflux for 3 hours, and then cooled and concentrated. The residue was suspended in water, adjusted to pH=7 by addition of 4N sodium hydroxide, and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4), filtered and stripped to give a red oil. The crude product was dissolved in methanol and silica gel was added. Following concentration, the coated silica gel was loaded onto a plug of silica gel and elution with ethyl acetate/hexanes yielded the title compound.
	With trichlorophosphate; In toluene; for 3h;Heating / reflux;	Method 0 Preparation of 4-Chloro-5-iodopyrimidine 5-Iodo-4(3H)-pyrimidinone (1 eq. ) was suspended in toluene to which was added POC13 (2.0 eq. ). The reaction mixture was heated to reflux for 3 hours, and then cooled and concentrated. The residue was suspended in water, adjusted to pH=7 by addition of 4N sodium hydroxide, and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgS04), filtered and stripped to give a red oil. The crude product was dissolved in methanol and silica gel was added. Following concentration, the coated silica gel was loaded onto a plug of silica gel and elution with ethyl acetate/hexanes yielded the title compound.

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2419 - 2422.
[2]Patent: WO2005/16914,2005,A1 .Location in patent: Page/Page column 44.
[3]Patent: WO2014/60432,2014,A1 .Location in patent: Page/Page column 139; 140.
[4]Patent: CN104744446,2019,B .Location in patent: Paragraph 0857; 0860-0862.
[5]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 2719 - 2724.
[6]Patent: US2002/52375,2002,A1 .
[7]Patent: WO2005/97162,2005,A2 .Location in patent: Page/Page column 527; 553; 554; 556.
[8]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1902 - 1906.
[9]Chemistry - A European Journal,2020,vol. 26,p. 1525 - 1529.

4
[ 63558-65-6 ]
[ 1066-54-2 ]
[ 111079-22-2 ]

References: [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 2719 - 2724.

5
[ 124-41-4 ]
[ 63558-65-6 ]
[ 219915-13-6 ]