반응 #56789

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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

수율 88.1%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도the resulting solution was refluxed for 1.5 hours
2. 2
   온도reflux
3. 3
   기타The reaction was quenched by addition of MeOH (25 mL)
4. 4
   농축After concentration
5. 5
   기타the residue was purified by column chromatography on silica gel with ethyl acetate/hexanes 1/1

실험 절차

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+).

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