Dimethylformamide → HCID 86609537, compound

Participants

Reaction Steps

To a stirred solution of 2-methanesulfonyl-4,6-dimethyl-pyrimidine-5-carboxylic acid (4-cyclopropylmethanesulfonyl-1-cyclopropylmethyl-cyclohexylmethyl)-amide (82 mg; 0.165 mmol) in DMF (2 ml) was added sodium cyanide (12 mg; 0.247 mmol) and the mixture was stirred at room temperature for 90 minutes. The mixture was evaporated in vacuo, coevaporating with toluene, to give an orange oil. The oil was partitioned between EtOAc (20 ml) and water (20 ml). The organic phase was separated, washed with water (20 ml) and brine (20 ml), dried (MgSO4) and evaporated in vacuo to give a yellow oil. The crude product was purified by prep. TLC eluted with 50% EtOAc in hexane to give the product as a white foam (43 mg). 1H NMR (400 MHz, CDCl3): δ 5.96 (1H, t, J 6.2), 3.64 (2H, d, J 6.4), 2.99-2.93 (1H, m), 2.87 (2H, d, J 7.1), 2.57 (6H, s), 2.04-1.84 (6H, m), 1.47-1.39 (2H, m), 1.27-1.23 (2H, m), 1.16-1.08 (1H, m), 0.79-0.67 (3H, m), 0.55-0.51 (2H, m), 0.42-0.38 (2H, m), 0.05-0.03 (2H, m). m/z=445 (M+H+).

Provenance & Evidence