Reacción #84532

Ecuación de reacción

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

3-fluoro-4-morpholinoaniline

trimethylaluminium

→

title compound

Rendimiento 49.5%

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

Rendimiento 49.5%

Disolventes

DCM

DCM

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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:

Fuente