1,2,3,4-Tetrahydro-1-naphthylamine → 5,6-dimethyl-N2-(pyridin-2-ylmethyl)-N4-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrimidine-2,4-diamine

Participants

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 1,2,3,4-tetrahydronaphthalen-1-ylamine 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, DMSO-d6) δ ppm 1.60-1.69 (m, 3H), 1.83 (bs, 4H), 2.09 (s, 3H), 2.66-2.75 (m, 2H), 4.46 (d, J=5.37 Hz, 2H), 5.31 (bs, 1H), 6.33 (d, J=8.33 Hz, 1H), 6.70-6.78 (m, 1H), 7.07 (dd, J1=15.31 Hz, J2=6.45 Hz, 4H), 7.15 (d, J=5.64 Hz, 1H), 7.26 (d, J=7.52 Hz, 1H), 7.64 (d, J=7.25 Hz, 1H), 8.42 (d, J=4.03 Hz, 1H); MS (ESI) m/z 361.0 (M+1)+.

Provenance & Evidence