Phosgene → HCID 22125024, compound

Participants

Reaction Steps

A solution of 1 g (2.3 mmol) of 5-(2,6-dichloroanilino)methyl-4-[3-(2-hydroxyethyl)phenyl]amino-2-methylthiopyrimidine in 60 ml of tetrahydrofuran was treated with 0.8 ml (6 mmol) of triethylamine and the mixture was added dropwise to a solution of 1.8 ml of phosgene (20% in toluene) in 40 ml of tetrahydrofuran. The cooling was removed. After 2 hours 100 ml of saturated aqueous ammonium chloride solution were added. The mixture was separated and the organic phase was dried over magnesium sulfate, filtered and evaporated. The residue was subjected to column chromatography on silica gel using diethyl ether/hexane (1:2) for the elution. Product-containing fractions were combined and evaporated to give 0.5 g (50%) of 3-(2,6-dichlorophenyl)-7-methylthio-3,4-dihydro-1-[3-(2-chloroethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid. [Mass spectrum (ESI) MH+ =479].

Provenance & Evidence