반응 #84524

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(Z)-methyl-3-(2-((3-fluorophenyl)thio)acetamido)but-2-enoate

3-fluoro-4-morpholinoaniline

trimethylaluminium

→

title compound

수율 67.0%

2-(((3-fluorophenyl)thio)methyl)-3-(3-fluoro-4-morpholinophenyl)-6-methyl-pyrimidin-4(3H)-one

수율 67.0%

용매

DCM

DCM

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후처리

1. 1
   workup.STIRRINGthe resulting mixture was stirred at rt for 12 h
2. 2
   기타The mixture was quenched with saturated NH4Cl aqueous solution
3. 3
   추출extracted with CH2Cl2 (50 mL×2)
4. 4
   세척The combined organic phases were washed with brine (100 mL)
5. 5
   건조dried over anhydrous Na2SO4
6. 6
   농축concentrated in vacuo
7. 7
   기타The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

실험 절차

To a solution of 3-fluoro-4-morpholinoaniline (0.54 g, 2.75 mmol) in DCM (15 mL) was added trimethylaluminium (4.8 mL, 9.60 mmol, 2 M in toluene) and the mixture was stirred at rt for 0.5 h. A solution of (Z)-methyl-3-(2-((3-fluorophenyl)thio)acetamido)but-2-enoate (0.78 g, 2.75 mmol) in DCM (5 mL) was added slowly and the resulting mixture was stirred at rt for 12 h. The mixture was quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×2). The combined organic phases were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale brown solid (0.79 g, 67%). The compound was characterized by the following spectroscopic data:

출처