3,3-Difluorocyclopentan-1-amine hydrochloride → N4-(3,3-difluorocyclopentyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Participants

Reaction Steps

The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using 3,3-difluorocyclopentylamine hydrochloride instead of cyclopentanamine. The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1), and then the final product was washed with diethyl ether to afford the titled compound as a white solid. 1H NMR (300 MHz, methanol-d4) δ ppm 1.73-2.27 (m, 9H), 2.36 (s, 3H), 3.30-3.34 (m, 2H), 4.30-4.40 (m, 1H), 7.73 (t, J=6.4, 1H), 7.84 (d, J=8.1, 1H), 8.28 (t, J=6.7, 1H), 8.70 (d, J=5.1, 1H); MS (ESI) m/z 334 (M+1)+.

Provenance & Evidence