Chloroacetonitrile → 2-Methylpentane

Participants

Reaction Steps

2-Chloro-4-(2-bromo-4-methylanilino)pyrimidine (500 mg, 1.68 mmol), chloroacetonitrile (0.13 ml, 2.02 mmol) and potassium carbonate (279 mg, 2.02 mmol) were dissolved in DMF (3 ml). The reaction mixture was stirred at room temperature for 12 hours. Chloroacetonitrile (0.13 ml, 2.02 mmol) and potassium carbonate (279 mg, 2.02 mmol) were again added, and the reaction mixture was stirred at room temperature for a further 48 hours. The reaction mixture was evaporated onto silica (5 ml) and purified by column chromatography eluting with EtOAc (0–40%):isohexane to give the title product as a solid on evaporation (537 mg). NMR (300 MHz): 2.38 (s, 3H), 4.82 (d, 1H), 4.99 (d, 1H), 6.09 (brs, 1H), 7.41 (m, 2H), 7.71 (s, 1H), 8.16 (brd, 1H); M.S. (ES+) 337.2 (MH+).

Provenance & Evidence