反応 #84532

反応方程式

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

3-fluoro-4-morpholinoaniline

trimethylaluminium

→

title compound

収率 49.5%

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

収率 49.5%

溶媒

DCM

DCM

反応条件

後処理

1. 1
   workup.STIRRINGthe resulting mixture was stirred at rt for 24 h
2. 2
   その他The mixture was quenched with saturated NH4Cl aqueous solution
3. 3
   抽出extracted with CH2Cl2 (50 mL×2)
4. 4
   洗浄The combined organic phases were washed with brine (100 mL)
5. 5
   乾燥dried over anhydrous Na2SO4
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The residue was purified by a silica gel column chromatography (EtOAc)

実験手順

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:

出典