Dimethylformamide → 4-Chlorothieno[3,2-d]pyrimidine

Temperature

0 °C

To a stirred solution of (COCl)2 (7.33 mL, 84.11 mmol) in anhydrous (CH2Cl)2 (20 mL) at 0° C. under nitrogen was added DMF (4.47 mL, 57.18 mmol). After 20 min a solution of thieno[3,2-d]pyrimidin-4(3H)-one (19) (4 g, 26.28 mmol) in anhydrous (CH2Cl)2 (5 mL) was added drop wise to the reaction mixture which was stirred for 20 min at 0° C., warmed to room temperature over another 20 min, heated at 80° C. for 1.5 hours, and cooled to room temperature. Finally, the reaction mixture was poured into water and extracted with DCM. The extract was washed sequentially with water, brine, dried over Na2SO4, filtered and evaporated to afford the title compound 20 (4.36 g, 97% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.02 (s, 1H), 8.59 (d, J=5.2 Hz, 1H), 7.75 (d, J=5.2 Hz, 1H).

1. temperaturewarmed to room temperature over another 20 min
2. temperatureheated at 80° C. for 1.5 hours
3. temperaturecooled to room temperature
4. extractionextracted with DCM
5. washThe extract was washed sequentially with water, brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated

ORD record

ord-c917e1178d09447f80b3ae6cd615da78

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08470850B2