69312-43-2|Isopropyl 2,4-dichloropyrimidine-5-carboxylate| Ambeed

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Quality Control of [ 69312-43-2 ] Purity: 95% SDS Specification

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Product Details of [ 69312-43-2 ]

CAS No. :	69312-43-2
Formula :	C₈H₈Cl₂N₂O₂
M.W :	235.07
SMILES Code :	O=C(C1=CN=C(Cl)N=C1Cl)OC(C)C
MDL No. :	MFCD28167986
InChI Key :	YRJUHXRUVTWBKE-UHFFFAOYSA-N
Pubchem ID :	57593543

Safety of [ 69312-43-2 ]

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

Computational Chemistry of [ 69312-43-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.38
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	52.95
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.08 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.13
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	2.78
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.35
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.	1.37
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	2.5
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.23

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.17
Solubility	0.16 mg/ml ; 0.000679 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.	-3.53
Solubility	0.0694 mg/ml ; 0.000295 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	-3.4
Solubility	0.0927 mg/ml ; 0.000394 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.	-5.76 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	0.0
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)	1.95

Application In Synthesis of [ 69312-43-2 ]

* 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 [ 69312-43-2 ]

[ 69312-43-2 ] Synthesis Path-Downstream 1~29

1
[ 67-63-0 ]
[ 2972-52-3 ]
[ 69312-43-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	In tetrahydrofuran; at 20℃;Cooling with ice;	21 g (100 mmol, 1.0 eq) of 2,4-dichloropyrimidine-5-formyl chloride was dissolved in 150 mL of anhydrous tetrahydrofuran, and 13.2 g (110 mmol, 2.2 eq) of isopropanol was slowly added dropwise under an ice bath,After the addition, the reaction system was warmed to room temperature overnight.The solvent was evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the product (18.3 g, yield = 81%).
	In tetrahydrofuran; at -40 - 20℃; for 2h;	To a precooled SOLUTION (-40C) of 2, 4-dichloropyrimidine-5-carbonyl chloride (5 ML) in tetrahydrofuran (20 ml) isopropanol (2.6 ml) was added dropwise. Then the reaction mixture was allowed to come to room temperature and stirred for 2h. After evaporation the residue was chromatographed on silica gel (dichloromethane/ethyl acetate) to yield the title compound (8.2 G). 1H NMR (300 MHz, CD03) : A/PPM = 1.40 (d, 6H, J = 7 Hz), 5.31 (m, 1 H), 9.0 (s, 1H)
	In tetrahydrofuran; at -78 - 20℃;	A solution of 2,4-dichloropyrimidine-5-carbonyl chloride (2.00 g, 9.45 mmol) in THF (4.7 mL) was cooled to -78 C before IPA (0.80 mL) was added. The mixture was warmed to rt and stirred overnight. The mixture was then concentrated in vacuo and purified by flash column chromatography on silica gel (0%? 10% EtOAc/heptane) to afford isopropyl 2,4-dichloropyrimidine- 5-carboxylate (A7) as a colorless oil.

References: [1]Patent: CN110790749,2020,A .Location in patent: Paragraph 0098; 0103-0106.
[2]Patent: WO2004/48343,2004,A1 .Location in patent: Page 99.
[3]Patent: WO2015/195228,2015,A1 .Location in patent: Paragraph 460.

2
[ 69312-43-2 ]
[ 46460-73-5 ]
[ 702679-42-3 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 20℃;	To a solution of 1-methylethyl 2, 4-dichloropyrimidine-5-carboxylate (4.7 G) and ethyldiisopropylamine (3.4 ml) in ACETONITRILE (250 ML) phenylmethyl [3- AMINOPROPYL] CARBAMATE (4.2 g) was added at 0C. Subsequently the reaction mixture was stirred over night at room temperature. After evaporation the residue was chromatographed on SILICA GEL (DICHLOROMETHANE/ISOPROPANOL) to yield the title compound (5.9 G). ESI-MS : 407 and 409 (M+)

References: [1]Patent: WO2004/48343,2004,A1 .Location in patent: Page 99.

3
[ 69312-43-2 ]
isopropyl 2-chloro-4-(imidazo[1,2-a]pyridin-3-yl)pyrimidine-5-carboxylate [ No CAS ]

References: [1]Patent: WO2015/195228,2015,A1 .

4
[ 120-72-9 ]
[ 69312-43-2 ]
isopropyl 2-chloro-4-(1H-indol-1-yl)pyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Indole (120 mg, 1 mmol) was dissolved in DMF (3 mL) and the mixture was treated with sodium hydride (45 mg, 1.1 mmol, 60% dispersion in oil) at 0 C for 15 min. Isopropyl 2,4- dichloropyrimidine-5-carboxylate (A7) (220 mg, 1.1 mmol) was added to the mixture and the resulting mixture was stirred at rt for 16 h. Subsequently, water was added and the mixture was concentrated in vacuo. The resulting residue was dissolved in EtOAc and water. The organic phase was isolated, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residue was then purified by flash column chromatography on silica gel (0%? 10% EtOAc/heptane) to afford methyl 2-chloro-4-(1 H-indol-1 -yl)pyrimidine-5-carboxylate as a white solid.

References: [1]Patent: WO2015/195228,2015,A1 .Location in patent: Paragraph 483.

5
[ 69312-43-2 ]
[ 111-34-2 ]
isopropyl (E)-4-(2-butoxyvinyl)-2-chloropyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; triethylamine; at 80℃; for 5h;	A mixture of <strong>[69312-43-2]isopropyl 2,4-dichloropyrimidine-5-carboxylate</strong> (50 mg, 0.21 mmol), 1- (vinyloxy)butane (63 mg, 0.63 mmol), palladium(ll) acetate (4 mg, 0.015 mmol), and TEA (0.032 mL), in PEG-400 (2 mL), was stirred at 80 C for 5 h. Upon cooling, the mixture was diluted with water and extracted with DCM. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (0 -> 10% EtOAc/heptane) to afford isopropyl (E)-4-(2-butoxyvinyl)-2- chloropyrimidine-5-carboxylate (A14).

References: [1]Patent: WO2015/195228,2015,A1 .Location in patent: Paragraph 467.

6
[ 69312-43-2 ]
[ 1426420-90-7 ]
isopropyl 2-chloro-4-(1-methyl-1H-indazol-3-yl)pyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 80℃; for 0.5h;	To a mixture of <strong>[69312-43-2]isopropyl 2,4-dichloropyrimidine-5-carboxylate</strong> (A7) (0.31 g, 1.32 mmol) and 1- methyl-3-(tributylstannyl)-1 H-indazole (A20) (0.67 g, 1.59 mmol), in 1 ,4-dioxane (24 mL), was added tris(dibenzylideneacetone)dipalladium(0) (0.60 g, 0.66 mmol). The resulting mixture was stirred at 80 C for 30 min. Upon cooling, the mixture was concentrated in vacuo, and the resulting residue was purified by flash column chromatography on silica gel (0 -> 20% EtOAc/heptane) to afford isopropyl 2-chloro-4-(1 -methyl-1 H-indazol-3-yl)pyrimidine-5-carboxylate (F7) as an off-white solid.

References: [1]Patent: WO2015/195228,2015,A1 .Location in patent: Paragraph 486.

7
[ 69312-43-2 ]
isopropyl 2-((4-(2-(dimethylamino)ethyl(methyl)amino)-2-methoxy-5-nitrophenyl)amino)-4-(1-methyl-1H-indol-3-yl)pyrimidine-5-carboxylate [ No CAS ]