Dimethylformamide dimethyl acetal → (4-Chlorophenyl)(pyrimidin-5-yl)methanone

Participants

Reaction Steps

7.7 g (0.065 mole) of N,N-dimethylformamide dimethyl acetal are added in portions to 10 g (0.055 mole) of 4-chlorophenyl hydroxyvinyl ketone (compare 1st stage) in 10 ml of toluene at 0° C. The reaction mixture is subsequently stirred for 15 minutes, and 5.7 g (0.055 mole) of formamidine acetate are then added. After further subsequent stirring for 15 minutes, a solution of 3 g (0.055 mole) of sodium methylate in 80 ml of ethanol is added dropwise and the mixture is subsequently stirred under reflux for 8 hours. The reaction mixture is allowed to cool and is poured onto 400 ml of water and extracted with toluene. The organic phase is washed with water, dried over sodium sulphate and concentrated. The residue is purified by column chromatography (ethyl acetate: cyclohexane =3:1; silica gel). 3.7 g (31% of theory) of 4-chlorophenyl 5-pyrimidinyl ketone of melting point 110°-112° C. are obtained.

Provenance & Evidence