4-(2-Bromophenoxy)pyrimidin-2-amine → 4-{2-[6-(2-Aminopyrimidin-5-yl)pyridin-3-yl]phenoxy}pyrimidin-2-amine
Reaction equation
Br[C:2]1[CH:15]=[CH:14][CH:13]=[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:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:31]=[N:32][C:33]([NH2:36])=[N:34][CH:35]=3)=[N:28][CH:29]=2)O1>>[NH2:36][C:33]1[N:34]=[CH:35][C:30]([C:27]2[N:28]=[CH:29][C:24]([C:2]3[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=3[O:4][C:5]3[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[N:6]=3)=[CH:25][CH:26]=2)=[CH:31][N:32]=1Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 88 using 4-(2-bromophenoxy)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 C19H15N7O, 357.13; m/z found, 358.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.91 (s, 2H), 8.68-8.59 (m, 1H), 8.03 (dd, J=6.9, 0.9, 1H), 7.97-7.89 (m, 1H), 7.83 (d, J=8.3, 1H), 7.60-7.53 (m, 2H), 7.52-7.44 (m, 1H), 7.35 (d, J=7.9, 1H), 6.53 (dd, J=6.9, 0.9, 1H).
Sources & evidence
- ORD record
- ord-c5d12513dd40474a83854b60eea428d9
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
Loading…