Benzenepentanoic acid → 5-Phenyl-pentanoic acid (5-cyano-pyrimidin-4-yl)-amide

Participants

Reaction Steps

Under an atmosphere of nitrogen, oxalyl chloride (961 mg) was added dropwise to a solution of 5-phenylvaleric acid (Fluka, 1.00 g) in CH2Cl2 (8 ml) and DMF (0.4 ml). After stirring at ambient temperature overnight, the mixture was slowly added at 0° C. to a solution of 4-aminopyrimidine-5-carbonitrile (Aldrich, 505 mg) in pyridine (8 ml). The mixture was stirred overnight at r.t., taken up in CH2Cl2, washed with water, and dried (Na2SO4). After filtration, the solvent was evaporated, and the title compound (1.00 g, 64%) was obtained from the residue by column chromatography (silica gel, eluent gradient n-heptane/ethyl acetate=100:0-60:40). MS: m/e=281.3 [M+H+]. 1H NMR (d6-DMSO): δ 1.60-1.80 (m, 4H), 2.55-2.60 (m, 2H), 3.14 (t, 2H), 7.14-7.29 (m, 5H), 9.17 (d, 2H), 11.34 (bs, 1H).

Provenance & Evidence