1-(1H-Pyrazol-5-yl)methanamine → N4-cyclohexyl-5,6-dimethyl-N2-(1H-pyrazol-5-ylmethyl)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 (1H-pyrazol-5-ylmethyl)amine instead of (pyridin-2-ylmethyl)amine. The product 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 light-yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.28-1.37 (m, 5H), 1.60-1.69 (m, 5H), 1.86 (s, 3H), 2.25 (s, 3H), 3.98 (d, J=10.74 Hz, 1H), 4.52 (d, J=4.82 Hz, 2H), 6.12 (s, 1H), 7.59 (s, 1H), 7.98 (s, 1H), 12.15 (bs, 1H); MS (ESI) m/z 301.5 (M+1)+.

Provenance & Evidence