Diethyl Sulfate → 2-(Dimethylamino)-6-ethoxypyrimidin-4(1H)-one

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Reaction Steps

155.2 g (1 mol) of 2-dimethylamino-4,6-dihydroxypyrimidine are added while stirring to 1000 cc of 1N sodium hydroxide solution 1N and the mixture is heated to 50° over a short period. 170 g (1.1 mol) of diethyl sulphate are subsequently added dropwise, over the course of 2 hours, at 40°-45°. During the dropwise addition the pH value is kept at between 7.5 and 8.0 by further addition of 1N sodium hydroxide solution. Approximately 500 cc of 1N sodium hydroxide solution are additionally required. The mixture is stirred at 40° for 6 hours, filtered off, washed with a small amount of water and dried at 90° in a high vacuum. The compound may be recrystallized from benzene. M.P. 194°-195°. The aqueous phase may be extracted with chloroform in order to obtain better yields. The chloroform solution is dried with sodium sulphate and after evaporation crystals are obtained which may be recrystallized from benzene.

Provenance & Evidence