Reacción #2384934

Ecuación de reacción

water

oxalyl chloride

Dimethyl formamide

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

→

4-chloro-thieno[3,2-d]pyrimidine

Rendimiento 76.0%

Disolventes

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroforming a white gel
2. 2
   Temperaturathe reaction mixture was heated to reflux
3. 3
   ExtracciónThe product was extracted into dichloromethane (3×100 mL)
4. 4
   Secadodried over sodium sulfate
5. 5
   Concentraciónconcentrated in vacuo

Procedimiento

Dimethyl formamide (6.6 mL, 85.4 mmol) in 50 mL of dichloroethane was cooled to 0° C. and oxalyl chloride (62 mL, 124 mmol, 2M in dichloromethane) was added slowly over several minutes forming a white gel. 3H-thieno[3,2-d]pyrimidin-4-one (5.90 g, 38.8 mmol) was added and the reaction mixture was heated to reflux. After 2.5 hours the mixture was cooled to room temperature and poured into water. The product was extracted into dichloromethane (3×100 mL), dried over sodium sulfate, and concentrated in vacuo to afford 5.01 g (76%) of 4-chloro-thieno[3,2-d]pyrimidine. 1H NMR (400 MHz, DMSO) d 8.99 (s, 1H), 8.55 (d, 1H), 7.71 (d, 1H). LC-MS: 171 (MH+); HPLC RT: 2.85 minutes.

Fuente