Phosgene → HCID 22125090, compound

Participants

Reaction Steps

A solution of 3.3 g (5 mmol) of 4-[3-(2-(tert-butyldiphenylsilyloxy)ethyl)phenyl]amino-5-(2-chloro-6-methylanilino)methyl-2-methylthiopyrimidine in 50 ml of tetrahydrofuran was treated with 1.4 ml (10 mmol) of triethylamine and the resulting mixture was added dropwise to a solution of 5 ml (9.6 mmol) of phosgene (20% in toluene) in 30 ml of tetrahydrofuran. The mixture was stirred at room temperature for 24 hours and then heated at reflux for a further 18 hours. The mixture was cooled and evaporated. The mixture was partitioned between 40 ml of dichloromethane and 40 ml of saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 1.58 g (47%) of 1-[3-(2-(tert-butyldiphenylsilyloxy)ethyl)phenyl]-3-(2-chloro-6-methylphenyl)-3,4-dihydro-7-methylthio-pyrimido[4,5-d]pyrimidin-2(1H)-one as a yellow solid. [Mass spectrum (ESI) MH+ =679].

Provenance & Evidence