2-(2-Bromophenoxy)pyrimidine → 5-{5-[2-(Pyrimidin-2-yloxy)phenyl]pyridin-2-yl}pyrimidin-2-amine
Reaction equation
Br[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][C:5]1[N:10]=[CH:9][CH:8]=[CH:7][N:6]=1.CC1(C)C(C)(C)OB([C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:30]=[N:31][C:32]([NH2:35])=[N:33][CH:34]=3)=[N:27][CH:28]=2)O1>>[N:6]1[CH:7]=[CH:8][CH:9]=[N:10][C:5]=1[O:4][C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=1[C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:34]=[N:33][C:32]([NH2:35])=[N:31][CH:30]=2)=[N:27][CH:28]=1Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 88 using 2-(2-bromophenoxy)pyrimidine 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 C19H14N6O, 342.12; m/z found, 343.1 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.97 (s, 2H), 8.70 (dd, J=2.3, 0.8, 1H), 8.48 (d, J=4.8, 2H), 8.06 (dd, J=8.3, 2.3, 1H), 7.85 (dd, J=8.3, 0.9, 1H), 7.58 (dd, J=7.6, 1.8, 1H), 7.56-7.50 (m, 1H), 7.48-7.41 (m, 1H), 7.30 (dd, J=8.0, 1.2, 1H), 7.10 (t, J=4.8, 1H).
Sources & evidence
- ORD record
- ord-9ea17f87ecd0439e8e6ce335bff1aacd
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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