Ether, ethyl ethynyl → [2-Chloro-5-((E)-2-ethoxy-vinyl)-pyrimidin-4-yl]-(2-methoxy-1,1-dimethyl-ethyl)-amine

HRID 82281

Reaction equation

Br[C:2]1[C:3]([NH:9][C:10]([CH3:15])([CH3:14])[CH2:11][O:12][CH3:13])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[B]1OC2C(=CC=CC=2)O1.[CH2:25]([O:27][C:28]#[CH:29])[CH3:26]>>[Cl:8][C:5]1[N:4]=[C:3]([NH:9][C:10]([CH3:15])([CH3:14])[CH2:11][O:12][CH3:13])[C:2](/[CH:26]=[CH:25]/[O:27][CH2:28][CH3:29])=[CH:7][N:6]=1

Participants

Reactant 3

HCID 61239Ether, ethyl ethynyl

HCID 6327445Benzcatechinborane

HCID 86672124(5-Bromo-2-chloro-pyrimidin-4-yl)-(2-methoxy-1,1-dimethyl-ethyl)-amine

Product 1

HCID 86672125[2-Chloro-5-((E)-2-ethoxy-vinyl)-pyrimidin-4-yl]-(2-methoxy-1,1-dimethyl-ethyl)-amine

Procedure

The title compound was prepared according to the method described for Preparation 61 using (5-Bromo-2-chloro-pyrimidin-4-yl)-(2-methoxy-1,1-dimethyl-ethyl)-amine (Preparation 256), catechol borane and ethoxyacetylene (40% in hexane) to afford the title compound as light brown gum in 44% yield, 2.6 g.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-1ce22986ba4a440495b30bf3ade47f58
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846698B2

Linked notes

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