Ethyl 3-oxo-4-phenylbutanoate → 2,6-dibenzyl-1H-pyrimidin-4-one

Participants

Reaction Steps

To a solution of sodium (1.84 g, 80 mmol) in ethanol (200 ml) was added phenylacetamidine hydrochloride (16.2 g, 95.0 mmol) and ethyl 4-phenylacetoacetate (15 g, 72.9 mmol). The mixture was heated under reflux with stirring for 5 days followed by cooling and evaporation in vacuo. Water (150 ml) was added to the residue causing a solid to precipitate which was filtered off and washed thoroughly with water and diethyl ether. Recrystallisation of the solid from a chloroform/hexane mixture afforded 6.9 g 2,4-di(phenylmethyl)-6-hydroxypyrimidine as a white solid. m.pt., 158°-160° C., M+ found: 276.

Provenance & Evidence