Acetonitrile → HCID 21690601, compound

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Reaction Steps

A mixture of 3-amino-5-methylthio-6-methylpyridin-2(1H)-one (0.201 g, 0.0013 mol), 2-chloromethylbenzoxazole (0.239 g, 0.0014 mol), diisopropylethylamine (0.181 g, 0.0014 mol), and acetonitrile (6 mL) was heated at reflux under nitrogen for 35 hours. The dark solids which had formed were removed by filtration (0.089 g), and the filtrate evaporated to dryness. The two fractions were combined and chromatographed on a 30 mm column containing 230-400 mesh silica gel (6 inches). The column was prepared with methylene chloride and the crude product applied in methylene chloride. Development of the column was with 2% 2-propanol/methylene chloride (500 mL), 5% 2-propanol/methylene chloride (500 mL), and 10% 2-propanol/methylene chloride (1000 mL). Concentration of the fractions containing the desired product gave 0.133 g (33.5% yield) of 3-[(2-Benzoxazolyl)methyl]amino-5-methylthio-6-methylpyridin-2(1H)-one m.p. 180°-181° C.

Provenance & Evidence