5-Fluoro-o-toluidine → N4-(5-fluoro-2-methylphenyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

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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 (5-fluoro-2-methylphenyl)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 white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.03 (s, 3H), 2.11 (s, 3H), 2.17 (s, 3H), 4.39 (d, J=1.6 Hz, 2H), 7.77-7.88 (m, 2H), 7.09-7.20 (m, 3H), 7.34 (d, J=9.8 Hz, 1H), 7.45 (s, 1H), 7.64 (t, J=7.5 Hz, 1H), 8.43 (d, J=2.8 Hz, 1H); MS (ESI) m/z 338.8 (M+1)+.

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