tert-Butyl methyl ether → Methyl 2-chloro-6-(1-ethoxyvinyl)pyrimidine-4-carboxylate

Temperatur

94 °C

Methyl 2,6-dichloropyrimidine-4-carboxylate (8.44 g, 40.77 mmol) and bis(triphenylphosphine)-palladium(II) chloride (0.572 g, 0.82 mmol) in DMF (80 mL) was degased. Tributyl(1-ethoxy-vinyl)tin (14.46 mL, 42.81 mmol) was added under argon. The mixture was heated at 94° C. for 1 h. The mixture was poured into a solution of potassium fluoride (30 g) in water (400 mL). MTBE (300 mL) was added and the mixture was stirred for 10 min. The mixture was filtered and the filter was washed with 200 mL of MTBE. The filtrate was washed with brine (100 mL), dried over sodium sulfate and the solvents were evaporated. The residue purified by column chromatography on silica eluting with DCM to give the title compound as a solid (7.40 g, 75%).

1. filtrationThe mixture was filtered
2. washthe filter was washed with 200 mL of MTBE
3. washThe filtrate was washed with brine (100 mL)
4. dry with materialdried over sodium sulfate
5. customthe solvents were evaporated
6. customThe residue purified by column chromatography on silica eluting with DCM

ORD-Eintrag

ord-04fc7098ba644efc9570b0c89b16e660

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09439904B2