Diisopropylethylamine → 5-Chloro-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(5-fluoropyridin-2-yl)ethyl)pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,5-dichloro-4-(5-cyclopropyl-1H-pyrazole-3-ylamino)pyrimidine (Method 7; 0.14 g, 0.518 mmol), 1-(5-fluoropyridin-2-yl)ethanamine (Method 4; 0.091 g, 0.648 mmol), and DIEA (0.11 ml, 0.648 mmol) in n-BuOH (2 ml) was heated in a sealed tube at 185° C. for 18 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane-EtOAc=1:2) to give the title compound as a white solid (0.070 g, 36%). 1H NMR (400 MHz) 12.51 and 12.09 (s, 1H), 9.65 (s, 1H), 8.48 (s, 1H), 8.38 (s, 1H), 8.02 and 7.93 (b, 1H), 7.64 (m, 1H), 7.41 (m, 1H), 5.93 and 5.80 (b, 1H), 5.06 (m, 1H), 1.83 (m, 1H), 1.45 (d, J=6.8 Hz, 3H), 0.95 (m, 1H), 0.84 (m, 1H), 0.74 (m, 1H), 0.63 (m, 1H). MS: Calcd.: 373. Found: [M+H]+374.

Provenance & Evidence