4-(Trifluoromethyl)benzylamine → N4-cyclohexyl-5,6-dimethyl-N2-[4-(trifluoromethyl)benzyl]pyrimidine-2,4-diamine
Reaction equation
Cl.[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11](NCC3C=CC=CN=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[F:25][C:26]([F:36])([F:35])[C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1>>[CH:2]1([NH:8][C:9]2[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=[C:11]([NH:32][CH2:31][C:30]3[CH:33]=[CH:34][C:27]([C:26]([F:35])([F:36])[F:25])=[CH:28][CH:29]=3)[N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1Participants
Procedure
The titled compound was synthesized according to the general procedure described for preparation of N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 1) using [4-(trifluoromethyl)benzyl]amine instead of (pyridin-2-ylmethyl)amine. The product 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 1.12-1.21 (m, 5H), 1.44-1.59 (m, 5H), 1.86 (s, 3H), 2.24 (s, 3H), 3.71 (d, J=10.74 Hz, 1H), 4.62 (d, J=4.82 Hz, 2H), 7.50-7.58 (m, 3H), 7.67 (d, J=8.11 Hz, 2H), 8.20 (t, J=5.15 Hz, 1H), 12.99 (bs, 1H); MS (ESI) m/z 379.1 (M+1)+.
Workup
- customThe titled compound was synthesized
- customThe product was purified by column chromatography
- washeluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1)
- washthe final product was washed with diethyl ether
Sources & evidence
- ORD record
- ord-a2674832953e4f349787954064b3bf89
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447051B2
Reaction notes
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