Trifluoroacetic acid → 5-Amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile

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Reaction Steps

To a suspension of 5-[(2,4-dimethoxybenzyl)amino]-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile (240 mg, 0.62 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (0.96 mL, 12.5 mmol) dropwise, and the reaction mixture was stirred for 10 minutes. The reaction mixture was diluted with ethyl acetate and aqueous saturated sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-65% ethyl acetate/hexanes, linear gradient) to afford 5-amino-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile. MS ESI calc'd for C13H14N5 [M+H]+ 240. found 240. 1H NMR (500 MHz, DMSO-d6) δ 8.59 (s, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.36 (d, J=2.2 Hz, 1H), 6.57 (s, 1H), 6.55 (s, 1H), 6.25 (s, 2H), 2.28 (s, 3H), 2.18 (s, 3H).

Provenance & Evidence