p-Toluenesulfonic acid → 4-(6-Bromo-2-methyl-benzoimidazol-1-yl)-[1,3,5]triazin-2-ylamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-N-(2-amino-5-bromophenyl)-1,3,5-triazine-2,4-diamine (2.50 g, 8.89 mmol) in methanol (25 mL) and THF (100 mL) was added trimethyl orthoacetate (16.77 ml, 133.4 mmol) and TsOH (153.14 mg, 0.89 mmol). The reaction mixture was stirred at 70° C. for 1 hr then allowed to cool to RT overnight. Saturated aqueous sodium bicarbonate (30 mL) was introduced and the resulting precipitous solution filtered. The filtrate was extracted into DCM (3×100 mL extractions). The combined organic extracts were washed with brine (30 mL), dried (Na2SO4), filtered and concentrated in vacuo. The orange/yellow solid residue was then triturated from a mixture of DCM and MeOH to give the title compound as a pale yellow powder (400 mg): 1H NMR (500 MHz, DMSO) delta 2.89 (3H, s), 7.46 (1H, dd, J=8.5, 1.9 Hz), 7.57 (1H, d, J=8.4 Hz), 8.02 (1 H, s), 8.10 (1H, s), 8.61 (1H, d, J=1.8 Hz), 8.64 (1H, s); LC-MS: m/z=+306.7 (M+H)+.

Provenance & Evidence