Diisopropylaniline → N4-(2,6-diisopropylphenyl)-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 (2,6-diisopropylphenyl)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 1.13 (d, J=32.78 Hz, 12H), 2.12 (s, 3H), 2.31 (s, 3H), 3.00-3.12 (m, 2H), 4.40 (d, J=5.10 Hz, 2H). 5.40 (s, 1H), 5.65 (s, 1H), 6.85 (s, 1H), 7.04 (bs, 1H), 7.19 (d, J=7.52 Hz, 2H), 7.20-7.30 (m, 1H), 7.42 (t, J=7.52 Hz, 1H), 8.43 (d, J=4.03 Hz, 1H); MS (ESI) m/z 390.5 (M+1)+.

Provenance & Evidence