Reacción #56791

Ecuación de reacción

ethyl 4-bromobutyrate

compound 7h

3-[2(R)-amino-2-phenylethyl]-5-(2-chloro-3-methoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione

Na2CO3

→

compound 7i

Rendimiento 53.4%

3-[2(R)-{ethoxycarbonylpropyl-amino}-2-phenylethyl]-5-(2-chloro-3-methyoxyphenyl)-1-[2-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H) -dione

Rendimiento 53.4%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to room temperature
2. 2
   Otropartitioned between ethyl acetate and H2O
3. 3
   LavadoThe organic layer was washed with brine
4. 4
   Secadodried over Na2SO4
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe residue was purified by column chromatography on silica gel with ethyl acetate/hexanes/triethylamine 500/500/5

Procedimiento

To a solution of compound 7h (2.0 g, 3.65 mmol) in DMF (8 mL) was added Na2CO3 (0.47 g, 4.38 mmol) followed by ethyl 4-bromobutyrate (0.83 mL, 5.48 mmol). The mixture was heated at 95° C. for 1.5 hours, cooled to room temperature, and partitioned between ethyl acetate and H2O. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel with ethyl acetate/hexanes/triethylamine 500/500/5 to afford compound 7i (1.29 g) as a white solid. MS (CI) m/z 662.2, 664.2 (MH+)

Fuente