3,4-Difluoroaniline → N4-(3,4-difluorophenyl)-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 (3,4-difluorophenyl)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 2.05 (s, 3H), 2.32 (s, 3H), 4.70 (d, J=5.5 Hz, 2H), 5.87 (bs, 1H), 6.32 (bs, 1H), 6.95-7.05 (m, 2H), 7.16 (t, J=7.0 Hz, 1H), 7.32 (d, J=8.1 Hz, 1H), 7.57-7.66 (m, 2H), 8.58 (d, J=3.6 Hz, 1H); MS (ESI) m/z 342.7 (M+1)+.

Provenance & Evidence