3-Fluoro-2-methylaniline → N4-(3-fluoro-2-methylphenyl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine
Reaction equation
C1(N[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:8]=2)CCCC1.[F:23][C:24]1[C:25]([CH3:31])=[C:26]([NH2:30])[CH:27]=[CH:28][CH:29]=1>>[F:23][C:24]1[C:25]([CH3:31])=[C:26]([NH:30][C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:8]=2)[CH:27]=[CH:28][CH:29]=1Participants
3
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 (3-fluoro-2-methylphenyl)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 1.94 (s, 3H), 2.06 (s, 3H), 2.14 (s, 3H), 4.32 (bs, 2H), 6.76 (bs, 1H), 6.86-6.95 (m, 1H), 7.01-7.13 (m, 3H), 7.17 (t, J=6.4 Hz, 1H), 7.63 (t, J=8.4 Hz, 1H), 7.75 (s, 1H), 8.43 (d, J=4.2 Hz, 1H); MS (ESI) m/z 338.2 (M+1)+.