3-Methoxybenzylamine → N4-cyclohexyl-N2-(3-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 (3-methoxybenzyl)amine instead of (pyridin-2-ylmethyl)amine. The crude product was purified by crystallization from ethanol (10 mL) to afford the titled compound as the hydrochloride salt as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.15-1.28 (m, 5H), 1.60-1.80 (m, 5H), 1.87 (s, 3H), 2.21 (s, 3H), 3.72 (s, 3H), 3.86 (s, 1H), 4.48 (d, J=5.64 Hz, 2H), 6.75-6.89 (m, 3H), 7.23 (t, J=7.93 Hz, 1H), 7.56 (d, J=7.52 Hz, 1H), 8.40-8.55 (m, J=38.95 Hz, 1H), 12.56 (s, 1H); MS (ESI) m/z 341.5 (M+1)+.

Provenance & Evidence