Water → HCID 68105238, compound

Temperature

122.5 °C

To 2.9 g of 5-chloro-2-methoxypyrimidin-4-amine, 2.35 mL of ethyl acrylate, 18 mL of triethylamine, and 0.46 g of bis(tri-tert-butylphosphine)palladium(0) were added, and the mixture was stirred at an external temperature of 115 to 130° C. for 5 hours in a sealed tube. Thereto were further added 5 mL of triethylamine, 0.30 g of bis(tri-tert-butylphosphine)palladium(0) and 0.5 mL of ethyl acrylate, and the mixture was stirred at an external temperature of 120 to 130° C. for 6 hours 30 minutes in a sealed tube. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted with chloroform and ethyl acetate. The organic layer and the extract were combined, the resultant solution was 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=1:1 to obtain 0.89 g of ethyl (2E)-3-(4-amino-2-methoxypyrimidin-5-yl)acrylate as a yellow solid.

1. stirringthe mixture was stirred at an external temperature of 120 to 130° C. for 6 hours 30 minutes in a sealed tube
2. temperatureThe reaction mixture was cooled to room temperature
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with chloroform and ethyl acetate
5. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled off under reduced pressure
7. customThe resultant residue was purified by silica gel column chromatography

ORD record

ord-b6bcd4c3ea3b4089a61519b34dbe6073

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367831B2