Reaktion #1891186

Reaktionsgleichung

2-chloro-3,5-dimethylpyrazine

1-Boc-piperazine

2-(dicyclohexylphosphino)-2′,4′,6′-tri-isopropyl-1,1′-biphenyl

sodium tert-butoxide

→

3′,5′-dimethyl-2,3,5,6-tetrahydro[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester

Ausbeute 87.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was refluxed for 8 hr
2. 2
   TemperaturAfter cooling
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with saturated brine
5. 5
   Sonstigethe solvent was evaporated
6. 6
   SonstigeThe residue was purified by column chromatography (hexane:ethyl acetate)

Vorschrift

To a mixture of 2-chloro-3,5-dimethylpyrazine (2.8 g), 1-Boc-piperazine (3.7 g), palladium (II) acetate (225 mg), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (953 mg) and sodium tert-butoxide (2.7 g) was added toluene (40 mL), and the mixture was refluxed for 8 hr. After cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate) to give 3′,5′-dimethyl-2,3,5,6-tetrahydro[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (5 g). 3′,5′-Dimethyl-2,3,5,6-tetrahydro[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (5 g) was dissolved in chloroform (15 mL), 4N hydrogen chloride/ethyl acetate (15 mL) was added, and the mixture was stirred at room temperature overnight. Ethyl acetate (100 mL) was added, and the mixture was filtered to give the title compound (3.3 g).

Quelle