Diethyl Ether → 4-Chloro-6-(1-ethoxyvinyl)pyrimidine

Temperature

80 °C

4,6-Dichloropyrimidine (1.0 g, 6.71 mmol), bis(triphenylphosphine)palladium(II) chloride (0.094 g, 0.134 mmol) and tributyl[1-(ethyloxy)ethenyl]stannane (2.449 mL, 7.25 mmol) were added together in DMF (25 mL) and the resulting mixture was heated at 80° C. under argon for 18 hours. The reaction mixture was allowed to cool to room temperature and poured into an aqueous solution of potassium fluoride (5.7 g in 57 mL water). Diethyl ether (80 mL) was added and the solid was filtered, washed with diethyl ether (×2) and discarded. The filtrate was separated and the organic layer was washed with water, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-20% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a white solid (564 mg);

1. temperatureto cool to room temperature
2. filtrationthe solid was filtered
3. washwashed with diethyl ether (×2)
4. customThe filtrate was separated
5. washthe organic layer was washed with water
6. customdried under magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by column chromatography (Biotage SP4)
9. washeluting with a gradient of 0-20% ethyl acetate and iso-hexane
10. additionProduct containing fractions
11. customevaporated under reduced pressure

ORD record

ord-844f1176d3df4a2b9213078e8191a284

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796283B2