4-Fluoro-2-methylaniline → N4-(4-fluoro-2-methylphenyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)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-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 2.01 (s, 3H), 2.07 (s, 3H), 2.15 (s, 3H), 4.30 (bs, 2H), 6.68 (bs, 1H), 6.84-6.89 (m, 1H), 6.98-7.10 (m, 2H), 7.17 (t, J=7.3 Hz, 2H), 7.57-7.67 (m, 2H), 8.43 (d, J=4.2 Hz, 1H); MS (ESI) m/z 338.8 (M+1)+.

Provenance & Evidence