2-[4-(5-Bromo-2-methoxybenzyl)-1-piperazinyl]pyrimidine → 4-Phenyl-2-[(4-(2-pyrimidinyl)-piperazinyl)methyl]anisole

Participants

Reaction Steps

A solution of 182 mg 2-[(4-(2-pyrimidinyl)-piperazinyl)methyl]-4-bromoanisole in 1 mL of tetrahydrofuran heated to 60° C. and 6 mg of Pd(PPh3)4 was added. To this mixture 0.5 mL of a 1 M solution of phenylmagnesium bromide in tetrahydrofuran was added dropwise. The reaction mixture was heated at relux temperature under nitrogen for 1 hr, cooled to room temperature and the solvent removed by evaporation under reduced pressure to yield 4-phenyl-2-[(4-(2-pyrimidinyl)-piperazinyl)methyl]anisole which was purified by chromatography on silica gel using 5% methanol in dichloromethane as eluent. Evaporation of the solvent yielded 140 mg of a solid which was treated with ethyl acetate-HCl to give 50 mg of 4-phenyl-2-[(4-(2-pyrimidinyl)-piperazinyl)methyl]anisole dihydrochloride (Compound 1), mp 205-207° C.

Provenance & Evidence