5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → HCID 178508338, compound

HRID 1524095Notes

Reaction equation

Br[C:2]1[C:3]([O:8][C@H:9]2[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:16][C:17]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[CH:19][C:18]=1[C:32]1[CH:33]=[N:34][C:35]([NH2:38])=[N:36][CH:37]=1>>[NH2:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([O:8][C:3]2[C:2]([C:21]3[CH:20]=[CH:19][C:18]([C:32]4[CH:37]=[N:36][C:35]([NH2:38])=[N:34][CH:33]=4)=[C:17]([F:16])[CH:22]=3)=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:10][CH2:11]1

Participants

Reactant 2

HCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

HCID 178511711HCID 178511711, compound

Product 1

HCID 178508338HCID 178508338, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using trans-4-((3-bromopyridin-2-yl)oxy)cyclohexanamine 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 C21H22FN5O, 379.18; m/z found, 380.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.47 (d, J=1.1, 2H), 8.15 (dd, J=4.9, 1.7, 1H), 7.81 (dd, J=7.4, 1.7, 1H), 7.53 (m, 3H), 7.05 (dd, J=7.4, 5.0, 1H), 6.87 (s, 2H), 5.02 (m, 1H), 2.63 (m, 1H), 2.05 (m, 2H), 1.77 (m, 2H), 1.39 (m, 2H), 1.18 (m, 4H).

Sources & evidence

ORD record: ord-2872ef4fd7cc402bb09cf8dfdf6e4d17
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079866B2

Reaction notes

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