N,N-Dimethylaniline → HCID 18982107, compound

Participants

Reaction Steps

A mixture of 4-ethoxy-5-(2-furanylcarbonyl)amino-6-hydroxy-2-methylpyrimidine (2.07 g, 7.87 mM), phosphorus oxychloride (30 ml) and dimethylaniline (1.5 ml, 11.7 mM) was heated at reflux for one hour. After cooling, the excess phosphorus oxychloride was removed by distillation under reduced pressure. Ethanol was then added, and the mixture partitioned between methylene chloride and water. The organic layer was separated, washed with sodium bicarbonate, water, dilute hydrochloric acid, water, and dried. The solvent was then removed by distillation under reduced pressure. Ethanol (10 ml) was added and the solid filtered off. This solid was further purified by flash column chromatography eluting with ethyl acetate/hexane (1:3). There was thus produced 7-ethoxy-5-methyl-2-(2-furyl)-oxazolo[5,4-d]pyrimidine (1.49 g, 77% yield); m.p. 104°-105.5° C.

Provenance & Evidence