3-Isoxazolamine → 5,6-dimethyl-N4-(1,2-oxazol-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 isoxazol-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 2.08 (s, 3H), 2.35 (s, 3H), 4.74 (d, J=2.8 Hz, 2H), 5.97 (bs, 1H), 6.98 (s, 1H), 7.17 (t, J=6.4 Hz, 1H), 7.31-7.44 (m, 2H), 7.63 (t, J=6.5 Hz, 1H), 8.17 (s, 1H), 8.56 (d, J=4.6 Hz, 1H); MS (ESI) m/z 297.8 (M+1)+.

Provenance & Evidence