Thionyl Chloride → HCID 11243073, compound

Participants

Reaction Steps

42.0 g (158 mmol) of 3,4,5,6,7,8-hexahydro-3-(2-hydroxy)ethyl-7-methylpyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-one in 240 ml of 1,2-dichloroethane was heated to reflux and then 12.7 ml (175 mmol) of thionyl chloride in 20 ml of 1,2-dichloroethane were added dropwise. After rafluxing for 2 h, the mixture was allowed to cool and was poured into ice/water. After partitioning between methylene chloride and water at pH=10, the aqueous phase was back-extracted with methylene chloride. The combined organic phases were dried and concentrated. The crude product (40 g) was recrystallized from 400 ml of isopropanol. 30.5 g (68%) of product with melting point 159-161° C. were isolated.

Provenance & Evidence