2-Bromo-4-methylaniline → 2-Methylpentane

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloropyrimidine (1 g, 6.71 mmol), 2-bromo-4-methylaniline (1.25 g, 6.71 mmol) and di-isopropylethylamine (1.29 ml, 7.38 mmol) were dissolved in n-butanol (5 ml). The reaction mixture was heated at 120° C. for 12 hours, cooled and evaporated onto silica (5 ml). The residue was purified by column chromatography and eluted with EtOAc (30%):isohexane to give the title product as a solid on evaporation (1.01 g). NMR (300 MHz): 2.31 (s, 3H), 6.50 (d, 1H), 7.22 (dd, 1H), 7.36 (d, 1H), 7.55 (s, 1H), 8.09 (d, 1H), 9.61 (s, 1H); m/z: (ES+) 298.1 (MH+).

Provenance & Evidence