Reacción #1132855

Ecuación de reacción

2-phenyl-pyrimidine-4-carboxylic acid

1,1′-carbonyldiimidazole

ethyl potassium malonate

magnesium chloride

→

3-oxo-3-(2-phenyl-pyrimidin-4-yl)-propionic acid ethyl ester

Rendimiento 58.3%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter removal of the solvent, hydrochloric acid
2. 2
   workup.ADDITIONwas added
3. 3
   Otrothe resulting solution was partitioned between water and ethyl acetate
4. 4
   LavadoThe organic layer was washed with brine
5. 5
   Secadodried over sodium sulfate
6. 6
   OtroThe solvent was removed under reduced pressure
7. 7
   Otrothe residue was purified with silica gel column chromatography (eluent; hexane/ethyl acetate=2/1)

Procedimiento

A solution of 2-phenyl-pyrimidine-4-carboxylic acid (3.49 g, 17.4 mmol) and 1,1′-carbonyldiimidazole (2.86 g, 17.7 mmol) in tetrahydrofuran (100 ml) was stirred at 60° C. for 20 min. After cooling to room temperature, ethyl potassium malonate (3.28 g, 19.2 mmol) and magnesium chloride (2.48 g, 26.1 mmol) were added and the solution was stirred at 60° C. for 7 hours. After removal of the solvent, hydrochloric acid was added to adjust pH to 4 to 2, and the resulting solution was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified with silica gel column chromatography (eluent; hexane/ethyl acetate=2/1) to afford 3-oxo-3-(2-phenyl-pyrimidin-4-yl)-propionic acid ethyl ester (2.74 g, 58%).

Fuente