5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → (2R)-2-({3-[4-(2-Aminopyrimidin-5-yl)-3-fluorophenyl]pyridin-2-yl}oxy)propan-1-ol
Reaction equation
Br[C:2]1[C:3]([O:8][C@H:9]([CH3:12])[CH2:10][OH:11])=[N:4][CH:5]=[CH:6][CH:7]=1.[F:13][C:14]1[CH:19]=[C:18](B2OC(C)(C)C(C)(C)O2)[CH:17]=[CH:16][C:15]=1[C:29]1[CH:30]=[N:31][C:32]([NH2:35])=[N:33][CH:34]=1>>[NH2:35][C:32]1[N:33]=[CH:34][C:29]([C:15]2[CH:16]=[CH:17][C:18]([C:2]3[C:3]([O:8][C@H:9]([CH3:12])[CH2:10][OH:11])=[N:4][CH:5]=[CH:6][CH:7]=3)=[CH:19][C:14]=2[F:13])=[CH:30][N:31]=1Participants
3
Procedure
The title compound was prepared in a manner similar to that described in Example 88 using (R)-2-((3-bromopyridin-2-yl)oxy)propan-1-ol and 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine. MS (ESI): mass calcd. for C18H17FN4O2, 340.13; m/z found, 340.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.50 (d, J=1.4, 2H), 8.17 (dd, J=4.9, 1.9, 1H), 7.85 (dd, J=7.4, 1.9, 1H), 7.67-7.54 (m, 3H), 7.09 (dd, J=7.4, 4.9, 1H), 6.89 (s, 2H), 5.35-5.23 (m, 1H), 4.86 (t, J=5.4, 1H), 3.62-3.51 (m, 2H), 1.25 (d, J=6.3, 3H).
Sources & evidence
- ORD record
- ord-baa766f8e89d4023906711bb93b0791a
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079866B2
Reaction notes
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