Reacción #2025293

Ecuación de reacción

(+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine

N,N'-dicyclohexylcarbodiimide

4-pyrrolidinopyridine

dodecanic acid

→

(+)-2-{4-(1-dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidine

Rendimiento 94.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter completion of the reaction
2. 2
   Filtraciónthe precipitates were filtered off
3. 3
   workup.ADDITION200 ml of toluene were added
4. 4
   Lavadoby washing with water, 5% acetic acid, water, 5% aqueous sodium hydrogen carbonate solution and water in this order
5. 5
   SecadoAfter the organic phase was dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   OtroThe resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate)

Procedimiento

Into 20 ml of dichloromethane were dissolved 1.78 g (5 millimoles) of the (+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine obtained in Preparation Example [starting material compound (VI)] 70 and 1.2 g (6 millimoles) of dodecanic acid, and then 1.4 g of N,N'-dicyclohexylcarbodiimide and 0.1 g of 4-pyrrolidinopyridine were added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the precipitates were filtered off and 200 ml of toluene were added thereto, followed by washing with water, 5% acetic acid, water, 5% aqueous sodium hydrogen carbonate solution and water in this order. After the organic phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate) to obtain 2.53 g (yield: 94%) of (+)-2-{4-(1-dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidine. The physical values are shown in Table-1.

Fuente