Cesium carbonate → 1-(2-Chloro-4-pyrimidinyl)-3-ethyl-2-oxo-3-pyrrolidinecarbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2,4-Dichloropyrimidine	HCID 77531	—
Reactant	3-Ethyl-2-oxopyrrolidine-3-carbonitrile	HCID 55300209	—
Catalyst	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	1-(2-Chloro-4-pyrimidinyl)-3-ethyl-2-oxo-3-pyrrolidinecarbonitrile	HCID 117840738	63.4%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a mixture of 3-ethyl-2-oxopyrrolidine-3-carbonitrile (40 mg) obtained in Step H of Example 1, 2,4-dichloropyrimidine (86 mg), cesium carbonate (190 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (10 mg) in tetrahydrofuran (1 mL) was added tris(dibenzylideneacetone)dipalladium(0) (5 mg), and the mixture was stirred overnight at 100° C. The insoluble substance was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (46 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09187453B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-1edf98398d5d46be90992d32d3a9087f
Source note	uspto-grants-2015_11