Stannous chloride dihydrate → 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)aniline

Participants

Reaction Steps

To a suspension of 2-(4-nitrophenyl)benzo[4,5]imidazo[1,2-a]pyrimidine (58 mg, 0.20 mmol) in ethanol (3 mL) was added SnCl2.2H2O (361 mg, 1.6 mmol). The solution was refluxed for 1.5 hours and then the volatiles were removed under vacuum. The residue was dissolved in DCM, washed with 1 N NaOH, and then H2O. The DCM layer was dried with MgSO4. The crude product was purified on flash chromatography (silica gel, 5% MeOH/DCM) to provide T518 as a yellow solid (35 mg, 67%). 1H NMR (400 MHz, DMSO-d6) δ 5.94 (s, 2H), 6.70 (m, 2H), 7.34 (m, 1H), 7.47 (m, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.75 (m, 1H), 8.08 (m, 2H), 8.21 (m, 1H), 9.34 (d, J=7.6 Hz, 1H). MS (ESI): 261.1 (M+H+).

Provenance & Evidence