Dimethylformamide → 3-Benzyl-2-(dipropylamino)-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(dipropylamino)-5-mesityl-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (50 mg, 0.14 mmol) and dimethylformamide (3 ml) was added sodium hydride (60% in oil, 10 mg, 0.25 mmol) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 0.5 hour, to the mixture was added a solution of benzylchloride (64 mg, 0.50 mmol) and dimethylformamide (2 ml) at 0° C. and stirred for 0.5 hour. After stirring at room temperature for 1 hour, the mixture was heated at 80° C. After cooling to room temperature, the mixture was diluted with water (20 ml) and extracted with ethyl acetate (50 ml×3). The extracts were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (20:1) to give 11 mg (17%) of the title compound.

Provenance & Evidence