Toluene → Ethyl 2-(pyrimidinylamino)-4-(trifluoromethyl)-5-oxazolecarboxylate

Participants

Reaction Steps

A reaction vessel was charged with 50 ml toluene, 4 g (16.4 mmol) ethyl 2-chloro-4-trifluoromethyl-5-oxazolecarboxylate and 3.12 g (32.8 mmol) 2-aminopyrimidine. The reaction mixture was heated at a temperature of 100°-110° C. for 16 hours. The mixture was cooled to room temperature, diluted with ethyl ether, washed with 5% hydrochloric acid, and then washed with large amounts of water. The ether portion was dried over magnesium sulfate and then concentrated under reduced pressure to yield 3.14 g of a yellow oily-solid material. This material was recrystallized from an ethanol-water solution to provide a yellow solid material which was air dried at room temperature, then triturated in warm hexane, and finally recrystallized from ethanol-water solution to yield 2.06 g of a yellow solid material (m.p. 199°-205° C.) identified in Table I.

Provenance & Evidence