3-Aminophenol → N-(3-((6-amino-5-(4-(pyridin-2-yloxy)phenyl)pyrimidin-4-yl)oxy)phenyl)acrylamide

HRID 1522226Notes

Reaction equation

HRID 1522226 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1.CC1(C)C(C)(C)OB([C:26]2[CH:38]=[CH:37][C:29]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=3)=[CH:28][CH:27]=2)O1.[C:40](Cl)(=[O:43])[CH:41]=[CH2:42]>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:17][C:13]2[CH:12]=[C:11]([NH:10][C:40](=[O:43])[CH:41]=[CH2:42])[CH:16]=[CH:15][CH:14]=2)[C:2]=1[C:26]1[CH:38]=[CH:37][C:29]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 115683-AminophenolHCID 13140Acryloyl chlorideHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 672487012-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]pyridine

Product 1

HCID 86721815N-(3-((6-amino-5-(4-(pyridin-2-yloxy)phenyl)pyrimidin-4-yl)oxy)phenyl)acrylamide

Procedure

N-(3-((6-amino-5-(4-(pyridin-2-yloxy)phenyl)pyrimidin-4-yl)oxy)phenyl)acrylamide was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)pyridine, and acryloyl chloride using methods A, C, and F. HPLC: 100%. MS: m/z=426 [M+H]+. 1H-NMR (DMSO-D6) δ 10.22 (s, 1H), 8.20 (d, 1H), 8.08 (s, 1H), 7.87 (t, 1H), 7.50 (s, 1H), 7.46 (d, 2H), 7.39 (d, 1H), 7.30 (t, 1H), 7.23 (d, 2H), 7.16 (m, 1H), 7.07 (d, 1H), 6.80 (d, 1H), 6.58 (broad s, 2H), 6.41 (dd, 1H), 6.25 (d, 1H), 5.76 (d, 1H).

Sources & evidence

ORD record
ord-b3f9fb4462cd4d39b0b19b725306ca75
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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