Diisopropylethylamine → 2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-nitropyridin-4-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-dichloro-5-nitropyridine (Method 91, 0.42 g, 2.18 mmol) and DIEA (0.46 ml, 2.61 mmol) in THF (10 ml) was added a 5-cyclopropyl-1H-pyrazol-3-amine (0.31 g, 2.50 mmol) solution in THF (5 ml) drop wise at 0° C. After addition, the reaction mixture was stirred at 25° C. for 17 hours. The solvent was removed under reduced pressure and the resulted residue was purified by column chromatography (hexane:EtOAc=3:1) to give the title compound as a yellow solid (0.54 g, 89%). 1H NMR (400 MHz) 12.55 (s, 1H), 9.95 (s, 1H), 8.97 (s, 1H), 8.09 (s, 1H), 6.02 (d, J=2.0 Hz, 1H), 1.93 (m, 1H), 0.97 (m, 2H), 0.71 (m, 2H). MS: Calcd.: 279; Found: [M+H]+ 280.

Provenance & Evidence