Réaction #84532

Équation de réaction

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

3-fluoro-4-morpholinoaniline

trimethylaluminium

→

title compound

Rendement 49.5%

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

Rendement 49.5%

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe resulting mixture was stirred at rt for 24 h
2. 2
   AutreThe mixture was quenched with saturated NH4Cl aqueous solution
3. 3
   Extractionextracted with CH2Cl2 (50 mL×2)
4. 4
   LavageThe combined organic phases were washed with brine (100 mL)
5. 5
   Séchagedried over anhydrous Na2SO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutreThe residue was purified by a silica gel column chromatography (EtOAc)

Mode opératoire

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:

Source