Acetonitrile → 2-Cyano-5-pyrimidinylcarbamoyl-beta-alanine

Participants

Reaction Steps

A solution of 0.83 g (7 mmol) of 2-cyano-5aminopyrimidine and 1 g (7 mmol) of beta-alanine ethyl ester isocyanate in 30 ml of anhydrous acetonitrile is heated for 4 hr at 70° C. The reaction mixture is concentrated to dryness and the residue is subjected directly to hydrolysis with 0.1 N HCl (50 ml) for 3 hr at 70° C. After cooling, the solution is treated with NaOH until a pH of 10 is obtained, washed with 3 × 40 ml of dichloromethane, acidified with HCl until a pH of 3 is obtained, and then concentrated to dryness in vacuum. The residue is treated with absolute ethanol whichpermits, by concentration of the ethanolic extract to dryness, 0.74 g (yield 45%) of 2-cyano-5-pyrimidinylcarbamoyl-beta-alanine to be obtained in the form of a solid having a melting point of 183° C.

Provenance & Evidence