반응 #84532

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(Z)-methyl-3-(4-(3-fluorophenoxy)butanamido)but-2-enoate

3-fluoro-4-morpholinoaniline

trimethylaluminium

→

title compound

수율 49.5%

3-(3-fluoro-4-morpholinophenyl)-2-(3-(3-fluorophenoxy)propyl)-6-methyl-pyrimidin-4(3H)-one

수율 49.5%

용매

DCM

DCM

반응 조건

후처리

1. 1
   workup.STIRRINGthe resulting mixture was stirred at rt for 24 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 (EtOAc)

실험 절차

To a solution of 3-fluoro-4-morpholinoaniline (0.36 g, 1.83 mmol) in DCM (20 mL) was added trimethylaluminium (2.7 mL, 5.40 mmol, 2 M in toluene) and the mixture was stirred at rt for 0.5 h. A solution of (Z)-methyl-3-(4-(3-fluorophenoxy)butanamido)but-2-enoate (0.80 g, 2.71 mmol) in DCM (4 mL) was added slowly and the resulting mixture was stirred at rt for 24 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 (EtOAc) to give the title compound as a pale yellow solid (0.40 g, 49%). The compound was characterized by the following spectroscopic data:

출처