2-(2-Bromophenoxy)pyrimidin-4-amine → 5-(5-{2-[(4-Aminopyrimidin-2-yl)oxy]phenyl}pyridin-2-yl)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[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][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>>[NH2:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([O:4][C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=2[C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:35]=[N:34][C:33]([NH2:36])=[N:32][CH:31]=3)=[N:28][CH:29]=2)[N:10]=1Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 88 using 2-(2-bromophenoxy)pyrimidin-4-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, 358.0 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.86 (s, 2H), 8.64 (dd, J=2.3, 0.8, 1H), 7.95 (dd, J=8.3, 2.3, 1H), 7.78-7.72 (m, 2H), 7.53-7.45 (m, 2H), 7.38 (m, 1H), 7.23 (dd, J=8.1, 1.2, 1H), 6.11 (d, J=5.9, 1H).
Sources & evidence
- ORD record
- ord-56309afd25404cd99fc293b511c9082d
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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