Thionyl Chloride → HCID 11243073, compound

Participants

Reaction Steps

42.0 g (158 mM) of 3-(2-hydroxyethyl)-7-methyl-5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-one in 240 ml of 1,2-dichloroethane were heated to reflux and then 12.7 ml (175 mM) of thionyl chloride in 20 ml of 1,2-dichloroethane were added dropwise. After refluxing for 2 h, the reaction mixture was allowed to cool and was poured into ice/water. The mixture was partitioned between methylene chloride and water at pH=10, and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried and then 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