3-Aminopyridine → 5,6-dimethyl-N4-(pyridin-3-yl)-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 pyridin-3-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, CDCl3) δ ppm 2.11 (s, 3H), 2.35 (s, 3H), 4.71 (d, J=3.0 Hz, 2H), 5.97 (bs, 1H), 6.41 (bs, 1H), 7.13-7.20 (m, 2H), 7.31 (d, J=7.4 Hz, 1H), 7.62 (t, J=7.6 Hz, 1H), 8.05 (d, J=4.0 Hz, 1H), 8.26 (bs, 1H), 8.56-8.63 (m, 2H); MS (ESI) m/z 307.9 (M+1)+.

Provenance & Evidence