35265-82-8|2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine| Ambeed

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Quality Control of [ 35265-82-8 ] Purity: 95% SDS Specification

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Product Details of [ 35265-82-8 ]

CAS No. :	35265-82-8
Formula :	C₇H₄Cl₂N₂S
M.W :	219.09
SMILES Code :	CC1=CC2=C(S1)C(Cl)=NC(Cl)=N2
MDL No. :	MFCD10000842
InChI Key :	ZDKZDOFEASCBMV-UHFFFAOYSA-N
Pubchem ID :	12724268

Safety of [ 35265-82-8 ]

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

Computational Chemistry of [ 35265-82-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	9
Fraction Csp3	0.14
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	52.4
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.53
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	3.63
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.31
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.	2.17
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	4.36
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.04
Solubility	0.02 mg/ml ; 0.0000911 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.45
Solubility	0.00773 mg/ml ; 0.0000353 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-4.22
Solubility	0.0131 mg/ml ; 0.0000597 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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	Yes
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.	-5.06 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<2.0
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)	2.48

Application In Synthesis of [ 35265-82-8 ]

* 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 [ 35265-82-8 ]

[ 35265-82-8 ] Synthesis Path-Downstream 1~35

1
[ 35265-82-8 ]
[ 76872-68-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium tetrahydroborate; ethanol; In tetrahydrofuran; at 0 - 20℃; for 16.0h;	2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine (10 g, 45.6 mmol) was dissolved in a mixed solution of tetrahydrofuran(100 mL) and ethanol (100 mL), the reaction solution was cooled to 0C, sodium borohydride (12.5 g, 198mmol) was added in batches. The reaction mixture was allowed to warm to room temperature and stirring was continuedfor 16 hours. The reaction mixture was diluted with water (500 mL) and then the pH was adjusted to 7 with 1 N aqueoushydrochloric acid solution. The aqueous phase was extracted with ethyl acetate (150 mL 3 3). The organic phase waswashed successively with water (100 mL x 3) and brine (100 mL), dried over anhydrous sodium sulfate, filtered and thefiltrate was concentrated under reduced pressure to delivera white solid45-e (7.5g, yield: 88%). This product was usedwithout further purification. LC-MS (ESI): m/z = 187 [M+H]+.
	With sodium tetrahydroborate; ethanol; In tetrahydrofuran; at 0 - 20℃; for 16.0h;	2,4-Dichloro-6-methylthieno[3,2-d]pyrimidine (10 g, 45.6 mmol) was dissolved in tetrahydrofuran (100 mL) and ethanol (100 mL). The reaction solution was cooled to 0 C. and sodium borohydride (12.5 g, 198 mmol) was added in portions. The reaction solution was warmed to room temperature and stirred for further 16 hours, then diluted with water (500 mL) and adjusted to pH=7 with 1N aqueous hydrochloric acid solution. The aqueous phase was extracted with ethyl acetate (150 mL3). The organic phase was washed with water (100 mL3) and brine (100 mL) successively, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to give 31-e as a white solid (7.5 g, yield 88%) which was used without further purification. LC-MS (ESI): m/z=187[M+H]+.

References: [1]Patent: EP3287463,2018,A1 .Location in patent: Paragraph 0326; 032.
[2]Journal of Medicinal Chemistry,1981,vol. 24,p. 376 - 382.
[3]Patent: US2018/208604,2018,A1 .Location in patent: Paragraph 0395-0396.

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate;Reflux;	General procedure: Synthesis of Compound 1-3 [0123] Compound 1-2 (1.34 g, 7.2 mmol) was dissolved in 20 ml phosphorus oxychloride and refluxed overnight. The reaction solution was poured into 200 ml ice water and stirred for 30 minutes. A large amount of solids was precipitated. The solids were filtered by suction, washed with water and dried, thereby obtaining the product 1-3 (1.12 g) in 69.7% yield. MS: 224.9[M+H]+.

3
[ 35265-82-8 ]
(2-Chloro-6-methyl-4H-thieno[3,2-d]pyrimidin-3-yl)-acetic acid ethyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 376 - 382.

4
[ 35265-82-8 ]
2-Methyl-5,9-dihydro-imidazo[1,2-a]thieno[3,2-d]pyrimidin-6-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 376 - 382.

5
[ 35265-82-8 ]
[ 1423-26-3 ]
2-chloro-6-methyl-4-[3-(trifluoromethyl)phenyl]thieno[3,2-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 2.0h;Heating / reflux;	To a toluene (10 mL)-water (1 mL) mixed solution of <strong>[35265-82-8]2,4-dichloro-6-methylthieno[3,2-d]pyrimidine</strong> (1.00 g, 4.56 mmol) were added 3-(trifluoromethyl)benzeneboronic acid (0.87 g, 4.56 mmol), sodium carbonate (0.97 g, 9.13 mmol), and tetrakis(triphenylphosphine)palladium (0.10 g, 5 mol%), followed by heating under reflux under a nitrogen stream for 2 hours. After completion of the reaction, the reaction liquid was poured into water and extracted with ethyl acetate. The resulting extract solution was washed with water and brine and then the solvent was removed by evaporation. The residue was purified on a silica gel column (Kiesel gel 60 manufactured by MERCK, 10% AcOEt-Hex) to obtain 2-chloro-6-methyl-4-[3-(trifluoromethyl)phenyl]thieno[3,2-d]pyrimidine (1.33 g, 89%). 1H-NMR (400MHz, CDCl3): 2.75(d, 3H, J=1.2Hz), 7.26(d, 1H, J=1.2Hz), 7.72(t, 1H, J=8.0Hz), 7.85(d, 1H, J=8.0Hz), 8.36(d, 1H, J=8.0Hz), 8.43(s, 1H). mp: 174-176C (dec.)

References: [1]Patent: EP1544202,2005,A1 .Location in patent: Page/Page column 49-50.

6
[ 35265-80-6 ]
[ 35265-82-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With trichlorophosphate; In DMF (N,N-dimethyl-formamide); at 100℃; for 2.0h;Heating / reflux;	Phosphorus oxychloride (6.85 g, 44.8 mmol) was added to a DMF (1 mL) solution of 2,4-dihydroxy-6-methylthieno[3,2-d]pyrimidine (2.72 g, 14.9 mmol), followed by heating under reflux at 100C for 2 hours. After completion of the reaction, the reaction liquid was poured into ice-water and precipitated crystals were collected by filtration. After the crystals were dissolved in ethyl acetate, the solution was washed with water and brine and then the solvent was removed by evaporation to obtain 2,4-dichloro-6-methylthieno[3,2-d]pyrimidine (3.21 g, 98%). 1H-NMR (400MHz, CDCl3): 2.73(d, 3H, J=1.2Hz), 7.20(q, 1H, J=1.2Hz). mp: 152-153C
	With N,N-dimethyl-aniline; trichlorophosphate; at 20 - 100℃; for 2.0h;	(2) To a mixture of 6-methylthieno[3,2-d]pyrimidine-2,4-diol (0.77 g) and phosphorus oxychloride (8 mL) was added N,N-dimethylaniline (1.6 mL) at room temperature, and the mixture was stirred at 100C for 2 h. The reaction solution was added dropwise to water with ice cooling, and the aqueous layer was extracted with chloroform. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform) to obtain 2,4-dichloro-6-methylthieno[3,2-d]pyrimidine (0.50 g). LC/MS: ESI+ (m/z) 219 (M++1) 1H-NMR (300 MHz, CDCl3): delta7.20-7.21 (m, 1H), 2.73 (d, J=1.2 Hz, 3H)

References: [1]Patent: EP1544202,2005,A1 .Location in patent: Page/Page column 49.
[2]Patent: EP2003131,2008,A1 .Location in patent: Page/Page column 64.

7
[ 175137-46-9 ]
[ 35265-82-8 ]
[ 927679-31-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine; In DMA; at 120℃;	Compound 4e was made from compound 4d (10.11 g, 46.13 mmol) and compound 1d (5.68 g, 46.13 mmol) using the same procedure of making compound 1e, 2-chloro-Lambda/-(5- cyclopropyl-1H-pyrazol-3-yl)thieno[3,2-d]pyrimidin-4-amine, from compound 1c and compound 1d. The title compound 4e was obtained as an off-white solid. (11.55g, 82%). 1H NMR (400MHz, DMSOd6): delta 0.68-0.72 (m, 2H), 0.92-0.96 (m, 2H), 1.88-1.95 (m, 1 H), 2.55 (s, 3H), 6.18 (S, 1H), 7.07 (s, 1 H), 10.29 (s, 1 H), 12.38 (s, 1 H). LCMS 306 (M+H). Anal. Calcd. For C13H12N5SCI.0.05 H2O.0.1 Et2O C, 51.24; H, 4.20; N, 22.30. Found: C, 51.20; H, 4.27; N, 22.05.

References: [1]Patent: WO2007/23382,2007,A2 .Location in patent: Page/Page column 65.

8
[ 35265-80-6 ]
[ 35265-82-8 ]

Yield	Reaction Conditions	Operation in experiment
41%	With trichlorophosphate; for 10.0h;Heating / reflux;	A mixture of 2,4-dihydroxy-6-methyl-thieno[3,2-d]pyrimidine 4c (45.14 g, 0.25 mol) and phosphorus oxychloride (500 ml) was refluxed for 10 h, whereby a clear brown solution was formed. The reaction mixture was cooled to room temperature and the excess of phosphorus oxychloride was evaporated in vacuo. The residue was poured into ice water and the aqueous mixture was extracted with chloroform. The organic phase was separated, washed with water until neutral and dried over magnesium sulfate. The final solution was passed through a silica gel plug. The solvent was evaporated in vacuo to yield 25.37 g of white solid. Recrystallizion from ethanol afforded 4d (22.5 g, 41%) as white needles. 1H NMR (CDCI3, 400 MHz) delta 7.13 (s, 1 H), 2.66 (s, 3H). 13C NMR (CDCI3, 100 MHz) delta 164.55, 156.48, 156.27, 154.62, 129.44, 122.70, 17.74.

References: [1]Patent: WO2007/23382,2007,A2 .Location in patent: Page/Page column 65.

9
[ 35265-82-8 ]
[ 124-40-3 ]
[ 952443-72-0 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; water; at 20℃; for 2.0h;	(1) To a solution of 50% aqueous dimethyl amine (0.15 g) in ethanol (5 mL) were added <strong>[35265-82-8]2,4-dichloro-6-methylthieno[3,2-d]pyrimidine</strong> (0.25 g) and triethylamine (0.12 g) at room temperature, and the mixture was stirred for 2 h. The reaction mixture was concentrated under reduced pressure and diluted with chloroform and water, and then the aqueous layer was extracted with chloroform. The organic layer was washed with 1 M hydrochloric acid and saturated brine and then dried with anhydrous magnesium sulfate, the desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure and crystallized with diethyl ether to obtain 2-chloro-N,N,6-trimethylthieno[3,2-d]pyrimidin-4-amine (0.16 g).

References: [1]Patent: EP2003131,2008,A1 .Location in patent: Page/Page column 49.

10
[ 35265-82-8 ]
[ 1429629-67-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With water; sodium hydroxide; In tetrahydrofuran; at 20℃;Inert atmosphere;	Step 1. Preparation of 2-Chloro-6-methylthieno[3,2-d]pyrimidin-4(3H)-oneA mixture of <strong>[35265-82-8]2,4-dichloro-6-methylthieno[3,2-d]pyrimidine</strong> (450 mg, 2.05 mmol), aqueous NaOH (IN, 4 mL) and THF (4 mL) was stirred at room temperature under N2. The reaction was monitored by HPLC until the reaction was completed. Then the mixture was neutralized to PH 5 by addition of 2N aqueous HC1. The solid was filtrated and dried to give 380 mg of 2-chloro-6- methylthieno[3,2-d]pyrimidin-4(3H)-one (yield was 92%) as a yellow solid. MS obsd. (ESI ) [(M+H)+]: 201.

References: [1]Patent: WO2013/53658,2013,A1 .Location in patent: Page/Page column 35.

11
[ 35265-82-8 ]
[ 1429629-68-4 ]

References: [1]Patent: WO2013/53658,2013,A1 .

12
[ 35265-82-8 ]
[ 1429629-57-1 ]

References: [1]Patent: US2013/90328,2013,A1 .
[2]Patent: WO2013/53658,2013,A1 .

13
[ 35265-82-8 ]
[ 1429629-67-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With water; sodium hydroxide; In tetrahydrofuran; at 20℃;Inert atmosphere;	A mixture of <strong>[35265-82-8]2,4-dichloro-6-methylthieno[3,2-d]pyrimidine</strong> (450 mg, 2.05 mmol), aqueous NaOH (1N, 4 mL) and THF (4 mL) was stirred at room temperature under N2. The reaction was monitored by HPLC until the reaction was completed. Then the mixture was neutralized to PH 5 by addition of 2N aqueous HCl. The solid was filtrated and dried to give 380 mg of 2-chloro-6-methylthieno[3,2-d]pyrimidin-4(3H)-one (yield was 92%) as a yellow solid. MS obsd. (ESI+) [(M+H)+]: 201.

References: [1]Patent: US2013/90328,2013,A1 .Location in patent: Paragraph 0198; 0199.

14
[ 35265-82-8 ]
[ 1429629-68-4 ]

References: [1]Patent: US2013/90328,2013,A1 .

15
[ 35265-82-8 ]
7-bromo-2,4-dichloro-6-methylthieno[3,2-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With aluminum (III) chloride; bromine; In acetic acid; at 80℃; for 6.0h;	[0151] To an acetic acid (15 mL) solution of 24-f (according to the synthesis procedure in the patent: WO 2007/023382A2) (992 mg, 4.6 mmol) and aluminum trichloride (1.23 g, 9.2 mmol) was slowly added a solution of bromine (0.72 mL,13.8 mmol) in acetic acid (5 mL) at room temperature. After dropwise addition, the reaction mixture was heated to 80Cand stirred for 6 hours. After cooling, the reaction mixture was poured into ethyl acetate (40 mL), washed with water (40mL), then 5% sodium thiosulfate solution (40 mL 3 2) to remove the color of bromine. The aqueous phase was extractedwith ethyl acetate (120 mL 3 2). The organic layers were combined and washed with saturated sodium bicarbonatesolution (100 mL) and saturated brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to givetitle compound 24-e (1.035 g, yield 76%) as a pale yellow solid. LC-MS (ESI): m/z 296.9 (M+H)+.
76%	With aluminum (III) chloride; bromine; In acetic acid; at 80℃; for 6.0h;	At normal temperature a solution of bromine (1.44 mE, 27.6 mmol) in acetic acid (10 mE) was slowly added dropwise into a solution of 8-g (prepared according to the method ofpatent: W02007/023382A2)(1.984 g, 9.2mmol) and aluminum trichloride (2.46 g, 18.4 mmol) in acetic acid (30 mE). The mixture was heated to 80 C. to react for 6 irs afier the addition was completed. The reaction mixture was cooled, and then partitioned between ethyl acetate (80 mE) and water (80 mE). The organic layer was separated and washed with 5% sodium thiosulfate solution (2x80 mE). The aqueous phase was extracted with ethyl acetate (x2), the combined organic phase was washed sequentially with saturated sodium bicarbonate solution (200 mE) and saturatedbrine (400 mE), dried over anhydrous sodium sulfate, and concentrated under reduced pressure, to yield target compound 8-f(1 .035 g, yield 76%) as a pale yellow solid. EC-MS (ESI): mlz 296.9 (M+H).

References: [1]Patent: EP2860181,2015,A1 .Location in patent: Paragraph 0150; 0151.
[2]Patent: US2016/214994,2016,A1 .Location in patent: Paragraph 0126; 0127.

16
[ 35265-82-8 ]
C₁₁H₇BrClN₅S [ No CAS ]