4-Aminobenzylamine → (4-Aminobenzyl)-(5,6-diphenylfuro[2,3-d]pyrimidin-4-yl)amine

Participants

Reaction Steps

4-Chloro-5,6-diphenylfuro[2,3-d]pyrimidine (0.10 g) and 4-(aminomethyl)aniline (0.05 g) in n-butanol (5 mL) were heated at 80° C. for 16 h. The reaction mixture was concentrated and the residue was partitioned between water and ethyl acetate. The organic layer was concentrated and the residue was purified by silica gel column chromatography using a mixture of dichloromethane:methanol (40:1), to give N-(4-aminobenzyl)-5,6-diphenylfuro[2,3-d]pyrimidin-4-amine (0.09 g, 70%). 1H NMR (300 MHz, CDCl3): δ 8.44 (s, 1H), 7.54-7.44 (m, 8H), 7.27-7.25 (m, 2H), 6.93 (d, 2H), 6.10 (d, 2H), 4.87 (t, 1H), 4.51 (d, 2H), 3.65 (brs, 2H). LC-MS (ESI) m/z 393.7 (M+H).

Provenance & Evidence