(4-Methylpyridin-2-yl)methanamine → N4-(4,4-difluorocyclohexyl)-5,6-dimethyl-N2-[(4-methylpyridin-2-yl)methyl]pyrimidine-2,4-diamine

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Reaction Steps

The titled compound was synthesized according to the general procedure described for preparation of N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 1) using [(4-methylpyridin-2-yl)methyl]amine instead of (pyridin-2-ylmethyl)amine and 2-chloro-N-(4,4-difluorocyclohexyl)-5,6-dimethylpyrimidin-4-amine (Step A) instead of 2-chloro-N-cyclohexyl-5,6-dimethylpyrimidin-4-amine. The product was purified by crystallization from ethanol to afford the titled compound (45% yield) as the hydrochloride salt as a light-yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.45-1.55 (m, 4H), 1.80-2.05 (m, 7H), 2.28 (s, 3H), 2.52 (s, 3H), 4.05 (bs, 1H), 4.99 (d, J=5.37 Hz, 2H), 7.65-7.78 (m, 3H) 8.31 (s, 1H), 8.67 (d, J=5.91 Hz, 1H), 13.42 (s, 1H); MS (ESI) m/z 362.4 (M+1)+.

Provenance & Evidence