Sodium Carbonate → 5-Chloro-1-(2-triphenylmethylaminothiazol-4-ylmethyl)pyrimidin-2-one

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 5-chloropyrimidin-2-one (688 mg), 4-chloromethyl-2-triphenylmethylaminothiazole (3.000 g), anhydrous sodium carbonate (1.086 g) and benzyltrimethylammonium chloride (20 mg) in dry N,N-dimethylformamide (25 ml) was heated at 90° C. After 1.5 h the reaction mixture was evaporated to dryness. The residue was suspended in ethyl acetate (250 ml) and washed with water (2×60 ml) and brine (60 ml), then dried and evaporated to a dark brown foam. The foam was subjected to column chromatography on silica developing and eluting with chloroform-ethanol, 24:1. This gave a brown foam which was triturated with diethyl ether to give a brown solid (2.03 g). A portion of the solid (360 mg) was recrystallised from ethyl acetate to give buff crystals of the title pyrimidinone (129 mg), m.p. 215°-216° C., λmax (EtOH) 268 nm (ε 8,630), 335 nm (ε 3,440).

Provenance & Evidence