Acryloyl chloride → (R)-4-(4-(4-((1-acryloylpyrrolidin-3-yl)methoxy)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile

HRID 1522261Notes

Reaction equation

Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[OH:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19]C(C)(C)C)=O)[CH2:13]1.CC1(C)C(C)(C)OB([C:32]2[CH:46]=[CH:45][C:35]([O:36][C:37]3[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=3)=[CH:34][CH:33]=2)O1.[C:48](Cl)(=O)[CH:49]=C>>[C:17]([N:14]1[CH2:15][CH2:16][C@@H:12]([CH2:11][O:10][C:7]2[C:2]([C:32]3[CH:46]=[CH:45][C:35]([O:36][C:37]4[CH:44]=[CH:43][C:40]([C:41]#[N:42])=[CH:39][CH:38]=4)=[CH:34][CH:33]=3)=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=2)[CH2:13]1)(=[O:19])[CH:48]=[CH2:49]

Participants

Reactant 4

HCID 13140Acryloyl chloride

HCID 1514340tert-Butyl (3R)-3-(hydroxymethyl)pyrrolidine-1-carboxylate

HCID 223468894-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]benzonitrile

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

Product 1

HCID 89266790(R)-4-(4-(4-((1-acryloylpyrrolidin-3-yl)methoxy)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile

Procedure

(R)-4-(4-(4-((1-acryloylpyrrolidin-3-yl)methoxy)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile was prepared from 5,6-dichloropyrimidin-4-amine, (R)-tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate, 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)benzonitrile, and acryloyl chloride using methods A, C, D, and F. HPLC: 99%. MS: m/z=442 [M+H]+.

Sources & evidence

ORD record: ord-d21a2a648d9144f397b5ec7200347c8b
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073947B2

Reaction notes

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