Реакция #84532

Уравнение реакции

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

3-fluoro-4-morpholinoaniline

trimethylaluminium

→

title compound

Выход 49.5%

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

Выход 49.5%

Растворители

DCM

DCM

Условия реакции

Обработка

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

Методика

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:

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