4-Amino-1-methylpiperidine → 5,6-dimethyl-N4-(1-methylpiperidin-4-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 1-methylpiperidin-4-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-grey solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.68 (bs, 4H) 1.85 (s, 3H) 2.13 (bs, 3H) 2.57 (bs, 3H) 2.66 (bs, 2H) 3.13 (d, J=11.82 Hz, 2H) 3.81 (bs, 1H) 4.52 (d, J=5.91 Hz, 2H) 6.52 (s, 1H) 7.15-7.22 (m, 1H) 7.27 (d, J=7.79 Hz, 1H) 7.70 (d, J=7.66 Hz, 1H) 8.48 (d, J=4.03 Hz, 1H); MS (ESI) m/z 327.5 (M+1)+.

Provenance & Evidence