5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → HCID 90313283, compound

HRID 1524093Notes

Reaction equation

HRID 1524093 reaction equation
Br[C:2]1[C:3]([O:8][CH:9]2[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[F:17][C:18]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[CH:20][C:19]=1[C:33]1[CH:34]=[N:35][C:36]([NH2:39])=[N:37][CH:38]=1>>[O:15]=[S:12]1(=[O:16])[CH2:13][CH2:14][CH:9]([O:8][C:3]2[C:2]([C:22]3[CH:21]=[CH:20][C:19]([C:33]4[CH:38]=[N:37][C:36]([NH2:39])=[N:35][CH:34]=4)=[C:18]([F:17])[CH:23]=3)=[CH:7][CH:6]=[CH:5][N:4]=2)[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amineHCID 90314095HCID 90314095, compound

Product 1

HCID 90313283HCID 90313283, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 4-((3-bromopyridin-2-yl)oxy)tetrahydro-2H-thiopyran 1,1-dioxide 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 C20H19FN4O3S, 414.12; m/z found, 415.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.51 (d, J=1.3, 2H), 8.21 (dd, J=4.9, 1.8, 1H), 7.90 (dd, J=7.4, 1.8, 1H), 7.64 (m, 1H), 7.58 (dd, J=12.4, 1.5, 1H), 7.53 (dd, J=8.0, 1.7, 1H), 7.16 (dd, J=7.4, 4.9, 1H), 6.89 (s, 2H), 5.42 (dd, J=6.3, 3.0, 1H), 3.21 (dd, J=14.5, 8.0, 2H), 3.09-3.01 (m, 2H), 2.34-2.24 (m, 4H).

Sources & evidence

ORD record
ord-380a6d788d3d453abf38334341379cd2
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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