4-Methoxybenzylamine → 4-N-(3-bromophenyl)-6-N-[(4-methoxyphenyl)methyl]pyrido[3,4-d]pyrimidine-4,6-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[(3-bromophenyl)amino]-6-fluoropyrido[3,4-d]pyrimidine (0.48 g) and 4-methoxybenzylamine (10.3 g) in ethanol (50 mL) was heated to 100° C. for 5 days. The resulting product was chromatographed on silica gel, eluting with CH2Cl2:EtOAc (3:1), to give 4-[(3-bromophenyl)amino]-6-[(4-methoxyphenyl)methylamino]pyrido[3,4-d]pyrimidine (0.18 g,) mp (aqueous methanol), 178-179.5° C. A 0.10 g portion of this was dissolved in 5 mL trifluoroacetic acid and heated under reflux for 1 hour, and the mixture was evaporated to dryness. The residue was partitioned between EtOAc and aqueous ammonia, and the crude product was chromatographed on alumina, eluting with CH2Cl2:MeOH (97:3) to give 6-amino-4-[(3-bromophenyl)amino]pyrido[3,4-d]pyrimidine (0.040 g,), mp (CH2Cl2) 241.5-242° C.

Provenance & Evidence