2,6-Lutidine → 2-Methylpentane

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloropyrimidine (596 mg, 4 mmol), methyl 2-aminobenzoate (517 ml, 4 mmol) and 2,6-lutidine (465 ml, 4 mmol) were dissolved in n-butanol (20 ml) with stirring. The reaction mixture was heated to 120° C. for 24 hours, allowed to cool to ambient temperature and evaporated onto silica (3 ml). The residue was purified by column chromatography eluting with EtOAc (0–20%): isohexane to give the title product as a colourless solid on evaporation (137 mg, 13%). NMR (CDCl3, 300 MHz): 3.97 (s, 3H), 6.63 (d, 1H), 7.09 (t, 1H) 7.61 (m, 1H), 8.05 (d, 1H), 8.19 (d, 1H), 8.74 (d, 1H); m/z: (ES+) 264.3 (MH+).

Provenance & Evidence