3-Aminophenol → HCID 86721845, compound

HRID 1522266Notes

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:27]=[N:28][N:29]([CH2:31][C:32]3[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=3)[C:35]([O:37][CH3:38])=[O:36])[CH:30]=2)O1.[C:43](Cl)(=[O:46])[CH:44]=[CH2:45]>>[C:43]([NH:10][C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=1)[O:17][C:7]1[C:2]([C:26]2[CH:27]=[N:28][N:29]([CH2:31][C:32]3[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=3)[C:35]([O:37][CH3:38])=[O:36])[CH:30]=2)=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=1)(=[O:46])[CH:44]=[CH2:45]

Participants

Reactant 4

HCID 115683-Aminophenol

HCID 13140Acryloyl chloride

HCID 242192625,6-Dichloro-pyrimidin-4-ylamine

HCID 70983115HCID 70983115, compound

Product 1

HCID 86721845HCID 86721845, compound

Procedure

methyl 3-((4-(4-(3-acrylamidophenoxy)-6-aminopyrimidin-5-yl)-1H-pyrazol-1-yl)methyl)benzoate was prepared from 5,6-dichloropyrimidin-4-amine, 3-aminophenol, methyl 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzoate, and acryloyl chloride using methods A, C, and F. HPLC: 94%. MS: m/z=471 [M+H]+. 1H-NMR (DMSO-d6) δ 10.20 (s, 1H), 8.18 (s, 1H), 7.99 (s, 1H), 7.94 (s, 1H), 7.89 (d, 1H), 7.74 (s, 1H), 7.59 (d, 1H), 7.53-7.49 (m, 2H), 7.41 (d, 1H), 7.31 (t, 1H), 6.81 (d, 1H), 6.65 (broad s, 2H), 6.42 (dd, 1H), 6.25 (d, 1H), 5.77 (d, 1H), 5.46 (s, 2H), 3.83 (s, 3H).

Sources & evidence

ORD record: ord-449a2f72e76b40ccaecef20f561081aa
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073947B2

Reaction notes

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