2,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamide → N-(5-amino-2-(2,6-dimethylpyrimidin-4-ylamino)pyridine-4-yl)-2,6-dichlorobenzamide

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Reaction Steps

To a solution of 2,6-dichloro-N-(2-(2,6-dimethylpyrimidin-4-ylamino)-5-nitropyridine-4-yl)benzoamide (0.057 g, 0.13 mmol) in dry ethanol (8 mL) was added palladium (0.015 g, 0.14 mmol) (10% on activated carbon powder, 50% water wet) in one portion at room temperature under N2. The resulting mixture was stirred under H2 balloon for 60 mins The mixture was filtered with Celite and the filtrate was concentrated by vacuum. The residue was purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give the desired product (9.8 mg, yield: 18%). 1H NMR (DMSO-d6, 400 MHz): δ 10.2 (d, J=24.6 Hz, 1H), 9.58 (s, 1H), 8.17 (d, J=28.7 Hz, 1H), 7.85 (s, 1H), 7.59 (s, 3H), 7.08 (s, 1H), 4.81 (s, 2H), 2.38 (s, 3H), 2.25 (s, 3H). LCMS (ESI) m/z: 403.0 [M+H+].

Provenance & Evidence