Cesium carbonate → 5-[(2,4-Dimethoxybenzyl)amino]-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a flask was added 5-bromo-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile (PrepEx 1.4) (500 mg, 1.65 mmol), Xantphos (95 mg, 0.17 mmol), Pd2(dba)3 (121 mg, 0.133 mmol) and cesium carbonate (1.08 g, 3.30 mmol). A solution of 2,4-Dimethoxybenzylamine (276 mg, 1.65 mmol) in degassed dioxane (16.5 mL) was added to the flask. The reaction was heated to 100° C. for one hour. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and water, and the organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-40% ethyl acetate/hexanes, linear gradient) to afford 5-[(2,4-dimethoxybenzyl)amino]-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carbonitrile. MS ESI calc'd for C22H24N5O2 [M+H]+ 390. found 390. 1H NMR (500 MHz, DMSO-d6) δ 8.62 (s, 1H), 7.71 (d, J=2.3 Hz, 1H), 7.43 (d, J=2.3 Hz, 1H), 7.21 (t, J=5.7 Hz, 1H), 7.08 (d, J=8.3 Hz, 1H), 6.57 (s, 1H), 6.54 (d, J=2.3 Hz, 1H), 6.53 (s, 1H), 6.45 (dd, J=2.3 Hz, 8.3 Hz, 1H), 4.16 (d, J=5.8 Hz, 2H), 3.73 (s, 3H), 3.70 (s, 3H), 2.18 (s, 3H), 2.15 (s, 3H).

Provenance & Evidence