Reaction #91412

Reaction equation

N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

(cyclopentylmethyl)amine

→

titled compound

N4-(cyclopentylmethyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Conditions

Workup

1. 1
   OtherThe titled compound was synthesized
2. 2
   OtherThe crude material was purified by column chromatography
3. 3
   Washeluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1)
4. 4
   Washthe final product was washed with diethyl ether

Procedure

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 (cyclopentylmethyl)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, DMSO-d6) δ ppm 1.00-1.09 (m, 2H), 1.30-1.38 (m, 2H), 1.38-1.49 (m, 4H), 1.80-1.94 (m, 4H), 2.26 (s, 3H), 3.14 (bs, 2H), 4.70 (bs, 2H), 7.37-7.42 (m, 2H), 7.91 (t, J=7.52, 1H), 8.09-8.13 (m, 1H), 8.43 (s, 1H), 8.55-8.62 (m, 1H), 12.65 (bs, 1H); MS (ESI) m/z 312.8 (M+1)+.

Source