HCID 61373381, compound → HCID 90314011, compound

HRID 1524096Notes

Reaction equation

HRID 1524096 reaction equation
Br[C:2]1[C:3]([O:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:15][C:16]1[CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=[CH:18][C:17]=1[C:31]1[CH:32]=[N:33][C:34]([NH2:37])=[N:35][CH:36]=1>>[F:15][C:16]1[CH:21]=[C:20]([C:2]2[C:3]([O:8][CH:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[N:4][CH:5]=[CH:6][CH:7]=2)[CH:19]=[CH:18][C:17]=1[C:31]1[CH:36]=[N:35][C:34]([NH2:37])=[N:33][CH:32]=1

Participants

3

Reactant 2

HCID 61373381HCID 61373381, compoundHCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine

Product 1

HCID 90314011HCID 90314011, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 3-bromo-2-((tetrahydro-2H-pyran-4-yl)oxy)pyridine 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 C20H19FN4O2, 366.15; m/z found, 367.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.47 (d, J=1.5, 2H), 8.15 (dd, J=4.9, 1.9, 1H), 7.84 (dd, J=7.4, 1.9, 1H), 7.64-7.48 (m, 3H), 7.07 (dd, J=7.4, 4.9, 1H), 6.86 (s, 2H), 5.30 (m, 1H), 3.81-3.72 (m, 2H), 3.49 (m, 2H), 1.98 (m, 2H), 1.70-1.55 (m, 2H).

Sources & evidence

ORD record
ord-c025fce50f834e9ead5334941fe54708
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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