3-Pyridinemethanamine → N4-cyclohexyl-5,6-dimethyl-N2-(pyridin-3-ylmethyl)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]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=CN=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[N:25]1C=CC=C(CN)[CH:26]=1>>[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:26]=[N:25][CH:22]=[CH:23][CH:24]=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 1-pyridin-3-ylmethanamine 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.) to afford the titled compound as the trifluoroacetate as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.08-1.34 (m, 5H), 1.50-1.61 (m, 3H) 1.62-1.69 (m, 2H), 1.87 (s, 3H), 2.23 (s, 3H), 3.71-3.79 (m, 1H), 4.63 (d, J=5.10 Hz, 2H), 7.60 (d, J=7.79 Hz, 1H), 7.64 (dd, J=7.66, 5.24 Hz, 1H), 8.05 (d, J=7.79 Hz, 1H), 8.62 (d, J=4.57 Hz, 1H) 8.62-8.69 (m, 1H) 8.71 (s, 1H), 12.61 (bs, 1H); MS (ESI) m/z 312.5 (M+1)+.
Workup
- customto afford the crude product
Sources & evidence
- ORD record
- ord-122adec734f34a259f60e884e8318488
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447051B2
Reaction notes
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