4-(2-Bromo-5-(trifluoromethyl)phenoxy)pyrimidin-2-amine → 4-{2-[6-(2-Aminopyrimidin-5-yl)pyridin-3-yl]-5-(trifluoromethyl)phenoxy}pyrimidin-2-amine
Reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[N:6]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[CH:30][C:31]([C:34]3[CH:35]=[N:36][C:37]([NH2:40])=[N:38][CH:39]=3)=[N:32][CH:33]=2)O1>>[NH2:40][C:37]1[N:38]=[CH:39][C:34]([C:31]2[N:32]=[CH:33][C:28]([C:2]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:3]=3[O:4][C:5]3[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[N:6]=3)=[CH:29][CH:30]=2)=[CH:35][N:36]=1Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 88 using 4-(2-bromo-5-(trifluoromethyl)phenoxy)pyrimidin-2-amine and 5-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidin-2-amine. MS (ESI): mass calcd. for C20H14F3N7O, 425.12; m/z found, 426.0 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.89 (s, 2H), 8.67 (dd, J=2.3, 0.8, 1H), 7.99 (d, J=5.6, 1H), 7.95 (dd, J=8.3, 2.3, 1H), 7.81 (dd, J=8.2, 0.9, 1H), 7.76-7.69 (m, 2H), 7.59 (s, 1H), 6.18 (d, J=5.8, 1H).
Sources & evidence
- ORD record
- ord-45cda3bc1cfb44d98911b603ea97a46e
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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