Benzylamine → 4-N-benzyl-6-chloropyrimidine-2,4-diamine

Participants

Reaction Steps

A mixture of 2-amino-4,6-dichloropyrimidine (0.5 g, 3.05 mmol), benzylamine (0.35 ml, 3.2 mmol), potassium carbonate (0.25 g, 1.81 mmol) and ethanol (15 ml) were heated to reflux for 16 h. The reaction mixture was cooled to room temperature and the solvents were removed under reduced pressure. The residue was triturated with ethyl acetate and the white product was collected by filtration. Concentration of the ethyl acetate filtrate also afforded a second crop of product. The combined solids were dried to give the required pyrimidine (0.36 g, 50%), m.p. 136° C.; δH (200 MHz, d6-DMSO) 4.55 (2H, br s, OCH2), 5.87 (1H, br s, C(5)H), 6.54 (2H, br s, NH2), 7.35-7.41 (5H, m, C6H5), 7.72 (1H, m, NH); m/z (+EI) 234 (M+, 85%), 106 (100), 91 (C6H5CH2+, 51%).

Provenance & Evidence