2-Chlorothieno[3,2-d]pyrimidine

2, 4-dichlorothieno[3, 2-d]pyrimidine (3, 1.19 g, 5.8 mmol) was taken up in ethanol (25 mL) and ethyl acetate (25 mL) to form a mixture. NaHC0To a solution of the dichloride (1 1.9g, 58mmol) in EtOAc (25OmL) and EtOH (25OmL) was added 10percent Pd/C (1.5g) and NaHCO2-Chlorothieno[3, 2-]pyrimidine (16).; To a solution of 15 (44.0 mg, 0.022 mmol) and NaHC0To a solution of 2, 4-dichloro-thieno[3, 2-d]pyrimidine 1 (300 mg, 1.46 mmol) in EtOAc, DIPEA (0.52 mL, 2.92 mmol) was added, followed by 10 percent Pd/C (300 mg) and the suspension shaken in a Parr hydrogenator at 45 psi of HCompoundII-25 (20.51g, 0.1mol, 1.0eq.), Acetic acid (34.3mL, 0.6mol, 6.0eq.) Andmethanol(150mL) placed in a reaction flask was added portionwise at 25 to zinc dust (26.16g, 0.4mol, 4.0eq.), The addition was completed temperaturewas raised to 70 For 3hours, TLC the reaction was complete. Cooling, filtration and the filter cakewas washed twice with methanol, and the filtrate sand column chromatography toobtain compoundI-25 was 11.12g, 63.23percent yield.2-Methoxythieno[3, 2-i/]pyrimidine (17).; To a solution of 16 (146 mg, 0.86 mmol) in MeOH (20 mL) was added NaOMe (130 mg, 2.41 mmol). The solution was heated at reflux for 37 h. An additional 1.4 equiv of NaOMe (65.0 mg) was added after 24 h (Note: The reaction was complete in 7 h with comparable yields when 4.2 equiv of NaOMe were added at the start of the reaction). The reaction mixture was cooled to room temperature, quenched with 1 N aq. HC1 (2.0 mL), and extracted with DCM (4 x 10 mL). The combined organic layers were washed with H20 (10 mL), dried (MgS04), and concentrated under reduced pressure to provide 17 (125 mg, 88%) as an off-white solid: Mp 167.0-168.5 C (DCM); IR (ATR, neat) 3071, 3025, 2917, 1558, 1528, 1478, 1379, 1295, 1249, 1031, 796, 677 cm'1; 1H NMR (DMSO- 6, 300 MHz) delta 9.30 (d, 1 H, J= 0.6 Hz), 8.45 (d, 1 H, J= 5.4 Hz), 7.47 (dd, 1 H, J= 5.4, 0.7 Hz), 3.96 (s, 3 H); 13C NMR (DMSO-d6, 75 MHz) delta 163.4, 162.4, 154.8, 139.9, 124.8, 122.9, 54.6; MS (EI) m/z 166 (M+, 29), 84 (100); HRMS (EI) m/z calcd for C7H6N2OS 166.0201, found 166.0201.

Molecular Weight:170.62
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Exact Mass:169.9705470
Monoisotopic Mass:169.9705470
Topological Polar Surface Area:54
Heavy Atom Count:10
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes