3-Fluorobenzylamine → N4-cyclohexyl-N2-(3-fluorobenzyl)-5,6-dimethylpyrimidine-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 (3-fluorobenzyl)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 1.08 (t, J=13.57 Hz, 1H), 1.19-1.31 (m, 4H), 1.58-1.70 (m, 5H), 1.87 (s, 3H), 2.22 (s, 3H), 3.82 (d, J=6.98 Hz, 1H), 4.53 (d, J=5.91 Hz, 2H), 7.01-7.11 (m, 2H), 7.14 (d, J=7.25 Hz, 2H), 7.32-7.39 (m, 1H), 7.56 (d, J=7.79 Hz, 1H), 8.35 (s, 1H), 12.47 (s, 1H); MS (ESI) m/z 329.0 (M+1)+.

Provenance & Evidence