m-Chloroperbenzoic acid → HCID 18778875, compound

Participants

Reaction Steps

A solution of 5-(3-Cyclopentyloxy-4-methoxyphenyl)pyrimidine (1.37 g) and 3-chloroperoxybenzoic acid (50.60%) (1.75 g) in dichloromethane (35 ml) was stirred at RT and the reaction followed by t.l.c. After 5 days, the reaction mixture was partitioned three times between dichloromethane (50 ml) and 10% aqueous Na2SO3 solution (50 ml). The combined organic phase was washed with 5% aqueous NaOH solution (3×30 ml), brine (30 ml), dried (MgSO4) and evaporated to afford a tan solid. Flash chromatography [SiO2 ; dichloromethane/EtOAc, 1:9 then dichloromethane/EtOAc/methane, 1:8:1] followed by recrystallisation from EtOAc furnished the title compound (390 g) as a white powder (mp 140°-143° C.). Found=C, 67.03; H, 6.31; N, 9.81. C16H18N2O3 requires C, 67.12; H, 6.34; N, 9.78%.

Provenance & Evidence