4-(Trifluoromethoxy)aniline → 5,6-dimethyl-N2-(pyridin-2-ylmethyl)-N4-[4-(trifluoromethoxy)phenyl]pyrimidine-2,4-diamine

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Reaction Steps

The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using [4-(trifluoromethoxy)phenyl]amine instead of cyclopentanamine. The crude material 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, CDCl3) δ ppm 2.07 (s, 3H), 2.34 (s, 3H), 4.70 (d, J=3.6 Hz, 2H), 5.92 (bs, 1H), 6.44 (bs, 1H), 7.01-7.21 (m, 3H), 7.16 (bs, 1H), 7.44-7.61 (m, 3H), 8.58 (bs, 1H); MS (ESI) m/z 390.7 (M+1)+.

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