Tetrabutylammonium Fluoride → HCID 22125111, compound

Participants

Reaction Steps

A solution of 1.2 g (1.7 mmol) of 7-anilino-1-[3-(2-(tert-butyldiphenyl-silyloxy)ethyl)phenyl]-3-(2-chloro-6-methylphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one in 30 ml of tetrahydrofuran was treated with 2.25 ml (2.25 mmol) of tetrabutylammonium fluoride (1M in tetrahydrofuran). The mixture was heated at reflux for 5 hours, cooled and evaporated. The residue was partitioned between 50 ml of ethyl acetate and 50 ml of 2M aqueous hydrochloric acid. The organic phase was washed with 40 ml of water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using a gradient elution from dichloromethane/methanol 100:1 to dichloromethane/methanol 100:5. Product-containing fractions were evaporated to give 350 mg (42%) of 7-anilino-3-(2-chloro-6-methylphenyl)-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a gum. [Mass spectrum (ESI) MH+ =486].

Provenance & Evidence