4-Methoxybenzylamine → N4-cyclohexyl-N2-(4-methoxybenzyl)-5,6-dimethylpyrimidine-2,4-diamine

Participants

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-methoxybenzyl)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 white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.10-1.13 (m, 1H), 1.24-1.35 (m, 3H), 1.62 (d, J=13.16 Hz, 1H), 1.72 (d, J=9.94 Hz, 4H), 1.87 (s, 3H), 2.22 (s, 3H), 3.72 (s, 3H), 3.94 (s, 1H), 4.46 (d, J=5.37 Hz, 2H), 6.88 (s, 2H), 7.26 (s, 2H), 7.57 (s, 1H), 8.01 (s, 1H), 12.66 (bs, 1H); MS (ESI) m/z 341.7 (M+1)+.

Provenance & Evidence