Dimethylformamide → 5-bromo-2-chloro-4-[(E)-2-ethoxyvinyl]pyrimidine

A mixture of 3.11 g of 5-bromo-2,4-dichloropyrimidine, 5.18 g of cis-1-ethoxy-2-tri-n-butylstannylethylene (synthesized according to the method disclosed in J. Am. Chem. Soc., 1977, 99, 7365), 0.479 g of dichlorobis(triphenylphosphine)palladium (II), and 60 mL of N, N-dimethylformamide was stirred for 6 hours at 70° C. After standing to cool, 60 mL of water, 60 mL of ethyl acetate, and 20 g of potassium fluoride were added thereto, and the mixture was stirred overnight at room temperature. The insolubles were filtered through celite and the filtrate was extracted with chloroform. The obtained organic layer was washed with water and saturated brine in that order, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: 10% chloroform-hexane/ethylacetate=100/0-0/100), to obtain 1.15 g of 5-bromo-2-chloro-4-[(E)-2-ethoxyvinyl]pyrimidine [11-1] (hereinafter, referred to as the compound [11-1]) as a pale yellow solid.

1. customsynthesized
2. temperatureto cool
3. filtrationThe insolubles were filtered through celite
4. extractionthe filtrate was extracted with chloroform
5. washThe obtained organic layer was washed with water and saturated brine in that order
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationThe insolubles were filtered
8. concentrationthe filtrate was concentrated under reduced pressure
9. customthe resulting residue was purified by silica gel column chromatography (eluent: 10% chloroform-hexane/ethylacetate=100/0-0/100)

ORD record

ord-af241d65e61e4705bfbe7475ee5917a7

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977336B2