Thionyl Chloride → HCID 22464638, compound

Participants

Reaction Steps

29.9 g (106 mmol) of 3-(2-hydroxyethyl)-5-methyl-6-dimethylcarbamoylthieno[2,3-d]pyrimidin-4-one in 200 ml of 1,2-dichloroethane were heated to reflux (slow dissolution), after which 12.7 ml (175 mmol) of thionyl chloride in 20 ml of 1,2-dichloroethane were added dropwise. After 1 h of reflux boiling, the reaction mixture was evaporated after it had been cooled down. The crude product was partitioned between methylene chloride and water at pH=9. After the organic phase had been dried and evaporated, 44.1 g (83%) of product were isolated as a dark oil, which was purified by column chromatography (silica gel, eluent ethyl acetate). 23.8 g (76%) of product, having a m.p. of 120-122° C., were isolated.

Provenance & Evidence