Benzylamine → N2-benzyl-N4-cyclohexyl-5,6-dimethylpyrimidine-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]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21]N=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:25](N)C1C=CC=CC=1>>[CH2:18]([NH:17][C:11]1[N:10]=[C:9]([NH:8][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2)[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:25]=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 benzylamine instead of (pyridin-2-ylmethyl)amine to afford the crude product. The solvent was removed by distillation, and the crude product was purified by HPLC (column: YMC-PACK ODS-AQ C18, 250 mm×20 mm, 10 μm; gradient: 20-50% acetonitrile in 0.02% trifluoroacetic acid/water over fifteen minutes; 50-100% acetonitrile in 0.02% trifluoroacetic acid/water over five minutes; flow rate: 25 mL/min; temperature: 25° C.). The titled compound was obtained as the trifluoroacetic acid salt as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.03-1.15 (m, 1H), 1.22-1.31 (m, 4H), 1.60 (d, J=12.63 Hz, 1H), 1.68 (s, 4H), 1.86 (s, 3H), 2.21 (s, 3H), 3.86-3.90 (m, 1H), 4.52 (d, J=5.64 Hz, 2H), 7.20-7.25 (m, 1H), 7.27-7.33 (m, 4H), 7.4 (bs, 1H), 8.02 (bs, 1H); MS (ESI) m/z 311.5 (M+1)+.
Workup
- customto afford the crude product
Sources & evidence
- ORD record
- ord-bcaa7738728e4bb2a91eea9b61310628
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447051B2
Reaction notes
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