Phosgene → HCID 22125179, compound

Participants

Reaction Steps

A solution of 2.6 g (4.9 mmol) of 5-(2-bromoanilino)methyl-4-[3-(2-(tetrahydropyranyloxy)ethyl)phenyl]amino-2-methylthiopyrimidine in 40 ml of tetrahydrofuran was treated with 2 ml (14.4 mmol) of triethylamine and the resulting solution added dropwise to an ice-cooled solution of phosgene (3 ml of a 20% solution in toluene, 5.8 mmol) in 40 ml of tetrahydrofuran. After 1 hour 50 ml of a saturated solution of ammonium chloride was added. The mixture was separated and the organic phase dried over magnesium sulfate and filtered. To the solution was added 20 ml of a saturated solution of hydrogen chloride in ethyl acetate. After 10 minutes the solution was evaporated to afford 1.8 g (78%) of 3-(2-bromophenyl)-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]-7-methylthio-pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid. [Mass spectrum (ESI) MH+ =471].

Provenance & Evidence