3-Methoxybenzylamine → 4-N-[(3-methoxyphenyl)methyl]pyrido[4,3-d]pyrimidine-4,7-diamine

Participants

Reaction Steps

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (136 mg, 0.71 mmol) (described in a previous experimental) and 3-methoxybenzylamine (1.37 g, 10.0 mmol) in isopropanol (3 mL) is stirred under N2 at reflux for 3 h. Evaporation of the solvent and chromatography on silica gel (5-10% EtOH/EtOAc) gives 7-amino-4-(3-methoxybenzylamino)pyrido[4,3-d]pyrimidine (153 mg, 77%) as a white solid. 1H NMR (DMSO) δ 9.11 (1H, s), 8.83 (1H, t, J=5.7 Hz), 8.26 (1H, s), 7.24 (1H, dt, Jd =0.8 Hz, Jt =8.1 Hz), 6.92 (2H, m), 6.81 (1H, dt, Jd =8.2 Hz, Jt =1.2 Hz), 6.46 (2H, brs), 6.37 (1H, s), 4.71 (2H, d, J=5.8 Hz), 3.73 (3H, s).

Provenance & Evidence