HCID 57531799, compound → N2-[(4-tert-butylpyridin-2-yl)methyl]-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:20]=3)[N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:25](C1C=CN=C(CN)C=1)([CH3:28])([CH3:27])[CH3:26]>>[C:25]([C:23]1[CH:22]=[CH:21][N:20]=[C:19]([CH2:18][NH:17][C:11]2[N:10]=[C:9]([NH:8][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]3)[C:14]([CH3:15])=[C:13]([CH3:16])[N:12]=2)[CH:24]=1)([CH3:28])([CH3:27])[CH3:26]Participants
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-tert-butylpyridin-2-yl)methyl]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 light-grey solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.02-1.10 (m, 3H), 1.24 (d, J=11.01 Hz, 11H), 1.42 (d, J=10.48 Hz, 2H), 1.55 (d, J=9.94 Hz, 3H), 1.90 (s, 3H) 2.29 (s, 3H), 3.43 (s, 1H), 4.71 (d, J=5.10 Hz, 2H), 7.52 (s, 2H) 7.59 (d, J=7.52 Hz, 1H), 8.21 (s, 1H), 8.53 (d, J=6.72 Hz, 1H), 12.48 (s, 1H); MS (ESI) m/z 368.1 (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-baeebb64cd2443b6b3e08d398ab19d78
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447051B2
Reaction notes
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