Water → HCID 57815271, compound

Temperature

125 °C

To a solution of 3.15 g of 3-chloro-6-methoxypyrazin-2-amine in 20 mL of triethylamine, 2.6 mL of ethyl acrylate and 0.50 g of bis(tri-tert-butylphosphine)palladium(0) were added, and the mixture was stirred at an external temperature of 120 to 130° C. for 2 hours in a sealed tube. Thereto was further added 5 mL of triethylamine, and the mixture was stirred at the same temperature for 4 hours 50 minutes. The reaction mixture was cooled to room temperature and left overnight, then 0.5 mL of ethyl acrylate and 0.25 g of bis(tri-tert-butylphosphine)palladium(0) were added thereto and the mixture was stirred at an external temperature of 115 to 125° C. for 9 hours 20 minutes in a sealed tube. The reaction mixture was cooled to room temperature, water and ethyl acetate were then added thereto, the organic layer was separated and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate=4:1 to obtain 2.55 g of ethyl (2E)-3-(3-amino-5-methoxypyrazin-2-yl)acrylate as a yellow solid.

1. stirringthe mixture was stirred at the same temperature for 4 hours 50 minutes
2. temperatureThe reaction mixture was cooled to room temperature
3. waitleft overnight
4. stirringthe mixture was stirred at an external temperature of 115 to 125° C. for 9 hours 20 minutes in a sealed tube
5. temperatureThe reaction mixture was cooled to room temperature
6. customthe organic layer was separated
7. extractionthe aqueous layer was extracted with ethyl acetate
8. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
9. dry with materialdried over anhydrous magnesium sulfate
10. distillationthe solvent was distilled off under reduced pressure
11. customThe resultant residue was purified by silica gel column chromatography

ORD record

ord-f6554002bad04346a980499ec23cffc0

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367831B2