4-[[2-Bromo-5-(trifluoromethyl)phenyl]methyl]morpholine → 5-{5-[2-(Morpholin-4-ylmethyl)-4-(trifluoromethyl)phenyl]pyridin-2-yl}pyrimidin-2-amine
Reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:16]=[N:17][C:18]([NH2:21])=[N:19][CH:20]=3)=[N:13][CH:14]=2)O1.Br[C:24]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:25]=1[CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>>[N:27]1([CH2:26][C:25]2[CH:33]=[C:34]([C:37]([F:39])([F:38])[F:40])[CH:35]=[CH:36][C:24]=2[C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[N:19][C:18]([NH2:21])=[N:17][CH:16]=3)=[N:13][CH:14]=2)[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 427 using 5-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)pyrimidin-2-amine and 4-(2-bromo-5-(trifluoromethyl)benzyl)morpholine. MS (ESI): mass calcd. for C21H20F3N5O, 415.16; m/z found, 416.0 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.96 (s, 2H), 8.67 (dd, J=2.3, 0.9, 1H), 7.97 (dd, J=8.2, 2.3, 1H), 7.89 (dd, J=8.2, 0.9, 1H), 7.86-7.84 (m, 1H), 7.72-7.65 (m, 1H), 7.52 (d, J=7.9, 1H), 3.63-3.58 (m, 4H), 3.54-3.48 (m, 2H), 2.41-2.28 (m, 4H).
Sources & evidence
- ORD record
- ord-2a645f99c196416db87a5b300cc0bd6d
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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