Reaction #56791

Reaction equation

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

Yield 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

Yield 53.4%

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   Otherpartitioned between ethyl acetate and H2O
3. 3
   WashThe organic layer was washed with brine
4. 4
   Dryingdried over Na2SO4
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified by column chromatography on silica gel with ethyl acetate/hexanes/triethylamine 500/500/5

Procedure

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+)

Source