Ammonia → 4-((4-Chlorobenzyl)oxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyrazin-6-yl)pyridin-2(1H)-one

https://huagongshe.com/reaction/2203017

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-one	HCID 57497864	—
Reactant	6-Bromo-2-cyclopropyl-3-methylimidazo[1,2-a]pyrazine	HCID 89690355	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	4-((4-Chlorobenzyl)oxy)-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyrazin-6-yl)pyridin-2(1H)-one	HCID 89691416	42.2%

Reaction Conditions

Temperature	150 °C

Reaction Steps

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (26.2 mg), 6-bromo-2-cyclopropyl-3-methylimidazo[1,2-a]pyrazine (42.1 mg), N,N′-dimethyl-1,2-ethanediamine (19.63 mg), CuI (21.2 mg), potassium carbonate (46.2 mg) and DMSO (1 ml) was heated at 150° C. for 1 h under microwave irradiation. The mixture was poured into 28% NH3 solution at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4, concentrated in vacuo, and purified by column chromatography (hexane/EtOAc) to give the title compound (19.1 mg) as pale yellow crystals.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09365540B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-4b0c648af6c746bb8a8f103e6087762e
Source note	uspto-grants-2016_06