4-Aminophenol → 4-(4-Hydroxyanilino)-6-chloropyrimidine

Participants

Reaction Steps

To a solution of 4,6-dichloropyrimidine (24.8 g), ethanol (250 ml) and triethylamine (51 ml) was added 4-aminophenol (18.2 g) and the solution was heated at reflux for 6 hours. After cooling the precipitate was collected, washed with DCM (100 ml) and recrystallized in acetonitrile to give the title compound (25.6 g, 69%) as crystals. NMR: 6.59 (1H, s), 6.73 (2H, d), 7.28 (2H, d), 8.33 (1H, s), 9.28 (1H, s), 9.52 (1H, s); m/z 222 (NH+).

Provenance & Evidence