Cesium carbonate → 5-Bromo-1-methyl-3-(pyrazin-2-ylamino)pyridin-2(1H)-one

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Aminopyrazine	HCID 78747	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	3,5-Dibromo-1-methylpyridin-2(1H)-one	HCID 3614350	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-Bromo-1-methyl-3-(pyrazin-2-ylamino)pyridin-2(1H)-one	HCID 86684085	47%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with pyrazin-2-amine (1.0 g, 10 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (2.7 g, 10 mmol), Pd2(dba)3 (460 mg, 0.50 mmol), XantPhos (600 mg, 1.0 mmol), cesium carbonate (6.52 g, 20 mmol), and 1,4-dioxane (150 mL). After three cycles of vacuum/argon flash, the mixture was heated at 100° C. for 2 h. It was then filtered and the filtrate was evaporated in vacuo. The residue was purified by recrystallization with methanol to afford 160a (1.3 g, 47%) as a light green solid. MS-ESI: [M+H]+ 281.0.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08669251B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-df48dad2ad3648cb86849d402a2482bd
Source note	uspto-grants-2014_03