Acryloyl chloride → 1-(trans-3-((6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-4-hydroxypyrrolidin-1-yl)prop-2-en-1-one

HRID 1522167Notes

Reaction equation

HRID 1522167 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][C@H:11]1[C@H:15]([OH:16])[CH2:14][N:13]([C:17]([O:19]C(C)(C)C)=O)[CH2:12]1.[O:24]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:40](Cl)(=O)[CH:41]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][C@H:11]2[C@H:15]([OH:16])[CH2:14][N:13]([C:17](=[O:19])[CH:40]=[CH2:41])[CH2:12]2)[C:2]=1[C:28]1[CH:29]=[CH:30][C:25]([O:24][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 11275699(3R,4R)-3-Amino-1-Boc-4-hydroxypyrrolidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 892666981-(trans-3-((6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-4-hydroxypyrrolidin-1-yl)prop-2-en-1-one

Procedure

1-(trans-3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-4-hydroxypyrrolidin-1-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, trans-tert-butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate, (4-phenoxyphenyl)boronic acid, and acryloyl chloride using methods B, C, D, and F. HPLC purity: 100%. MS: m/z=418 [M+H]+.

Sources & evidence

ORD record
ord-ac0be34026f34226a9705d7d029f6120
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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