4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 135670794, compound

Participants

Reaction Conditions

Reaction Steps

2-Allyloxybenzamidine (from sodium, 0.22 g, in ethanol, 100 ml, and 2-allyloxybenzamidine hydrochloride, 2.00 g) was dissolved in acetonitrile (50 ml) and the resulting cooled (2° C.) solution was added to a cooled (2° C.) solution of ethyl 4-chloro-2-methylthio-5-pyrimidine carboxylate (2.19 g) in acetonitrile (50 ml). The temperature was allowed to rise and the reaction mixture was stirred overnight at ambient temperature. The volume of the reaction mixture was reduced by evaporation under reduced pressure to yield a solid (0.96 g) which was collected. More product (0.45 g) precipitated from the filtrate. The combined products were recrystallized twice from ethanol to yield the title compound, 340 mg, m.p. 205-206° C.

Provenance & Evidence