1,3-Dimethyl 2-(4-chlorophenyl)propanedioate → 5-(4-Chlorophenyl)pyrimidine-4,6-diol

Participants

Reaction Steps

A solution of 18.90 g of 2-(4-chloro-phenyl)-malonic acid dimethyl ester in 200 ml of methanol was added dropwise at 0° C. to a solution of 14.60 g sodium methylate in 150 ml of methanol. The mixture was stirred for 1 h at 0° C. before 7.66 g of formamidine hydrochloride was added. The suspension was stirred at rt for 20 h. The solvent was removed and the residue was suspended in 200 ml 2 N aq. HCl. The pH of the suspension was carfully adjusted to 4-5 by adding 20 ml of 10 M NaOH, stirring was continued for 30 min. The white precipitate was collected, washed with water and diethyl ether and dried to give 16.44 g of 5-(4-chlorophenyl)-pyrimidine-4,6-diol as a white powder. LC-MS: tR=2.75 min, [M+H]+=222.96 (ES+), [M−H]−=220.92 (ES−).

Provenance & Evidence