Reacción #587937

Ecuación de reacción

thieno[3,2-d]pyrimidin-4(3H)-one

(COCl)2

DMF

→

title compound 20

Rendimiento 97.2%

4-Chlorothieno[3,2-d]pyrimidine

Rendimiento 97.2%

Disolventes

—

(CH2Cl)2

water

—

(CH2Cl)2

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawarmed to room temperature over another 20 min
2. 2
   Temperaturaheated at 80° C. for 1.5 hours
3. 3
   Temperaturacooled to room temperature
4. 4
   Extracciónextracted with DCM
5. 5
   LavadoThe extract was washed sequentially with water, brine
6. 6
   Secadodried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated

Procedimiento

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 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).

Fuente