Реакция #62875

Уравнение реакции

water

potassium fluoride

ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-chloropyrimidin-5-yl]-3-methylbutyrate

18-crown-6

→

ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-fluoropyrimidin-5-yl]-3-methylbutyrate

Выход 45.0%

Растворители

sulpholane

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling to the ambient temperature (ca. 22° C.)
2. 2
   Экстракцияextracted into ethyl acetate
3. 3
   ПромывкаThe organic layer was washed with water and brine
4. 4
   Другоеdried
5. 5
   Другоеthe solvent evaporated under reduced pressure
6. 6
   ДругоеThe residual brown liquid was purified by column chromatography on silica gel

Методика

A stirred suspension of dry potassium fluoride (1.41 g) and ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-chloropyrimidin-5-yl]-3-methylbutyrate (1.88 g) in dry sulpholane (14 cm3) in the presence of 18-crown-6 (0.38 g) was heated to 150° C. for a period of 24 hours, under an atmosphere of dry nitrogen. After cooling to the ambient temperature (ca. 22° C.), the reaction mixture was poured into water, and extracted into ethyl acetate. The organic layer was washed with water and brine, dried and the solvent evaporated under reduced pressure. The residual brown liquid was purified by column chromatography on silica gel, using dichloromethame as eluent, to give ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-fluoropyrimidin-5-yl]-3-methylbutyrate (0.8 g) as an orange liquid.

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