Tetrabutylammonium Fluoride → Pyrimido[4,5-d]pyrimidin-2(1H)-one

Participants

Reaction Steps

A solution of 200 mg (0.23 mmol) of 1-[3-(tert-butyldiphenylsilyloxyethyl)phenyl]-3-(2,4-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one in 5 ml of tetrahydrofuran was treated with 0.5 ml (0.5 mmol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran. After 1 hour the mixture was evaporated and the product purified by chromatography on silica gel using dichloromethane/methanol in a ratio 20:1 as eluting solvent. Evaporation of the product-containing fractions followed by trituration of the residue with hexane and filtration gave 60 mg (42%) 3-(2,4-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-[3-(2-hydroxyethyl))phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 110° C.

Provenance & Evidence