1-Naphthylamine → HCID 22125128, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 100 mg (0.22 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-1-phenyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one and 320 mg (2.2 mmol) of 1-aminonaphthalene was heated at 130° C. for 4 hours. The mixture was left to cool and was then partitioned between 10 ml of ethyl acetate and 2M hydrochloric acid. The insoluble 1-aminonaphthalene hydrochloride was removed by filtration. The ethyl acetate phase was separated, washed with 10 ml of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography on silica gel using ethyl acetate/hexane (1:1) for the elution. Product-containing fractions were evaporated to give 46 mg (40%) of 3-(2,6-dichlorophenyl)-3,4-dihydro-7-(1-naphthylamino)-1-phenylpyrimido[4,5-d]pyrimidin-2(1H)-one as a pale pink solid of melting point 213-214° C.

Provenance & Evidence