N,N-dimethyl-m-phenylenediamine → 4-N-[3-(dimethylamino)phenyl]pyrido[4,3-d]pyrimidine-4,7-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (245 mg, 1.28 mmol) (described in a previous experimental) and N,N-dimethyl-1,3-phenylenediamine (1.60 g, 11.8 mmol) is stirred under N2 at 190° C. for 1 h, and the resulting product is chromatographed (twice) over alumina (3% EtOH/CHCl3) to give 7-amino-4-(3-dimethylaminoanilino)pyrido[4,3-d]pyrimidine (113 mg, 32%) as a pale yellow solid. 1H NMR (DMSO) δ 9.66 (1H, brs), 9.33 (1H, s), 8.36 (1H, s), 7.22 (1H, brd, J=7.8 Hz), 7.16 (2H, m), 6.57 (2H, brs), 6.51 (1H, ddd, J=8.0, 2.3, 1.2 Hz), 6.42 (1H, s), 2.91 (6H, s).

Provenance & Evidence