Water → N-(4-amino-5-cyano-6-isopropoxypyridin-2-yl)-2-(2,5-dimethoxyphenyl)acetamide

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To a solution of 100 mg (0.520 mmol) of 4,6-diamino-2-isopropoxy-nicotinonitrile in 1 mL of pyridine was added 3 mL of CH2Cl2 followed by a solution of 150 mg (0.699 mmol) of 2,5-dimethoxyphenylacetyl chloride (prepared from (2,5-dimethoxyphenyl)acetic acid and oxalyl chloride in CH2Cl2) in 1 mL of CH2Cl2. The mixture was stirred at ambient temperature for 10 minutes then 1 mL of water was added, and the mixture was concentrated under reduced pressure. The residue was taken up in 20 mL of warm ethyl acetate and extracted with water (1×5 mL), 1M HCl(aq.) (2×5 mL), saturated NaHCO3(aq.) (2×5 mL), and brine (1×5 mL), dried over MgSO4, filtered, and concentrated to a solid. Recrystallization from methanol or 2-propanol provided 90 mg (47%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.06 (s, 1H), 7.10 (s, 1H), 6.90 (m, 1H), 6.84 (s, 2H), 6.79 (m, 2H), 5.28 (septet, 1H, J=6.1 Hz), 3.70 (s, 3H), 3.69 (s, 3H), 3.66 (s, 2H), 1.29 (d, 6H, J=6.1 Hz); MS (ESI) m/e=329 (M−Pr+H)+, 371 (M+H)+, 369 (M−H)−.

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