Tert-butyl 4-(2-(4-methoxybenzylamino)pyrimidin-4-yloxy)naphthalen-1-ylcarbamate → 4-(4-Aminonaphthalen-1-yloxy)pyrimidin-2-amine

Participants

Reaction Steps

A solution of impure tert-butyl 4-(2-(4-methoxybenzylamino)pyrimidin-4-yloxy)naphthalen-1-ylcarbamate described above (0.77 g, ˜50% purity, 0.8 mmol) in TFA (10 mL) was heated at reflux for 8 hr and then kept at RT for 16 hr. The reaction mixture was evaporated in vacuo and the residue was taken up into EtOAc and was washed with saturated aq NaHCO3 solution and with brine and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate in isohexane, 50-100%, gradient elution) to afford the title compound (111 mg, 54%) as a brown solid; m/z 253 (M+H)+, (ES+)+

Provenance & Evidence