Reaktion #56789

Reaktionsgleichung

5-(2-chloro-3-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

bis(trimethylsilyl)acetamide

2-fluoro-3-trifluoromethylbenzyl bromide

→

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

Ausbeute 88.1%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting solution was refluxed for 1.5 hours
2. 2
   Temperaturreflux
3. 3
   SonstigeThe reaction was quenched by addition of MeOH (25 mL)
4. 4
   EinengenAfter concentration
5. 5
   Sonstigethe residue was purified by column chromatography on silica gel with ethyl acetate/hexanes 1/1

Vorschrift

To a suspension of 5-(2-chloro-3-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione 7e (2.2 g, 8.7 mmol) in acetonitrile (25 mL) was added bis(trimethylsilyl)acetamide (4.3 mL, 17.4 mmol), and the resulting solution was refluxed for 1.5 hours. The mixture was cooled to room temperature, 2-fluoro-3-trifluoromethylbenzyl bromide (2.7 g, 10.5 mmol) was added, and reflux was resumed for 16 hours. The reaction was quenched by addition of MeOH (25 mL) and stirring for 2 hours. After concentration, the residue was purified by column chromatography on silica gel with ethyl acetate/hexanes 1/1 to afford 5-(2-chloro-3-methoxyphenyl)-1-[1-fluoro-6-(trifluoromethyl)benzyl]pyrimidine-2,4(1H,3H)-dione 7f (3.3 g, 88%) as a white solid. MS (CI) m/z 429.0, 431.0 (MH+).

Quelle