Reacción #2298648

Ecuación de reacción

5-[4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione

5-[4-[2-[4-Methyl-2-propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione

hydrogen

→

title compound

Rendimiento 92.0%

5-[4-[2-[4-methyl-2-Propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methyl]thiazolidine-2,4-dione

Rendimiento 92.0%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture was filtered through a bed of celite
2. 2
   OtroThe filtrate was evaporated to dryness under reduced pressure
3. 3
   Otropurified by column chromatography (2:1 EtOAc/petroleum ether as eluent)
4. 4
   Otrofollowed by crystallisation (CH2Cl2)

Procedimiento

A solution of 5-[4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydro-1-pyrimidinyl]ethoxy]phenyl methylene]thiazolidine-2,4-dione (5.0 g, 12.46 mmol) obtained from example 1 in 1,4-dioxane (75 ml) was reduced with hydrogen in the presence of 10% palladium on charcoal (12.0 g) at 60 psi pressure for 40 h. The mixture was filtered through a bed of celite. The filtrate was evaporated to dryness under reduced pressure, purified by column chromatography (2:1 EtOAc/petroleum ether as eluent) followed by crystallisation (CH2Cl2) to afford the title compound (4.6 g, 92%), mp 144-146° C.

Fuente