Acryloyl chloride → (R)-4-(4-(4-((4-acryloylmorpholin-2-yl)methoxy)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile

HRID 1522260Notes

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[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20]C(C)(C)C)=O)[CH2:13]1.CC1(C)C(C)(C)OB([C:33]2[CH:47]=[CH:46][C:36]([O:37][C:38]3[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=3)=[CH:35][CH:34]=2)O1.[C:49](Cl)(=O)[CH:50]=C>>[C:18]([N:14]1[CH2:15][CH2:16][O:17][C@@H:12]([CH2:11][O:10][C:7]2[C:2]([C:33]3[CH:47]=[CH:46][C:36]([O:37][C:38]4[CH:45]=[CH:44][C:41]([C:42]#[N:43])=[CH:40][CH:39]=4)=[CH:35][CH:34]=3)=[C:3]([NH2:9])[N:4]=[CH:5][N:6]=2)[CH2:13]1)(=[O:20])[CH:49]=[CH2:50]

Participants

Reactant 4

HCID 13140Acryloyl chloride

HCID 1512576(R)-N-Boc-2-hydroxymethylmorpholine

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 86721841(R)-4-(4-(4-((4-acryloylmorpholin-2-yl)methoxy)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile

Procedure

(R)-4-(4-(4-((4-acryloylmorpholin-2-yl)methoxy)-6-aminopyrimidin-5-yl)phenoxy)benzonitrile was prepared from 5,6-dichloropyrimidin-4-amine, (R)-tert-butyl 2-(hydroxymethyl)morpholine-4-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=458 [M+H]+.

Sources & evidence

ORD record: ord-4d41c1f9e5824dac94b2098cc50f1729
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073947B2

Reaction notes

Loading…