Potassium Carbonate → ethyl (2E)-3-(5-{[(3R)-1-cyclohexyl-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(R)-1-Cyclohexylpyrrolidin-3-amine dihydrochloride	HCID 53256313	—
Reactant	Ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate	HCID 86603667	—
Solvent	Dimethylformamide	HCID 6228	—
Product	ethyl (2E)-3-(5-{[(3R)-1-cyclohexyl-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate	HCID 86603694	47.2%

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of ethyl (2E)-3-(5-chloro-2-pyrazinyl)acrylate (416 mg) in DMF (10 mL) was added (3R)-1-cyclohexyl-3-pyrrolidinamine dihydrochloride (849 mg) and K2CO3 (1.35 g). After stirring for 2 hours at 120° C., the reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with H2O, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give ethyl (2E)-3-(5-{[(3R)-1-cyclohexyl-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylate (318 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07465731B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-55a94ffaedaf4d00b112d5be33cd5dab
Source note	uspto-grants-2008_12