N-(3-bromophenyl)-6-fluoropyrido[3,2-d]pyrimidin-4-amine → N-(3-bromophenyl)-6-methoxypyrido[3,2-d]pyrimidin-4-amine

Participants

Reaction Conditions

Reaction Steps

4-(3-Bromoanilino)-6-fluoropyrido[3,2-d]pyrimidine (described in a previous experimental) (0.11 g, 0.34 mmol) is added to a solution of NaOMe (prepared by the addition of Na metal (31 mg, 1.38 mmol) to dry MeOH (15 mL). After heating in a pressure vessel at 90° C. for 3 h, the solution is concentrated to dryness and the residue is partitioned between EtOAc and water. Workup of the organic portion gives 4-(3-bromophenyl) amino-6-methoxypyrido[3,2-d]pyrimidine (92 mg, 82%). 1H NMR (CDCl3) δ 8.73 (1H, s), 8.66 (1H, brs), 8.18 (1H, m), 8.05 (1H, d, J=8.9 Hz), 7.83-7.80 (1H, m), 7.30-7.24 (2H, m), 7.23 (1H, d, J=8.9 Hz), 4.12 (3H, s)

Provenance & Evidence