Реакция #84569

Уравнение реакции

N-(3-chloro-4-morpholinophenyl)-3-oxobutanamide

2-((4-chloronaphthalen-1-yl)oxy)acetamide

toluene

NH4Cl

→

title compound

Выход 56.4%

3-(3-chloro-4-morpholinophenyl)-2-(((4-chloronaphthalen-1-yl)oxy)methyl)-6-methylpyrimidin-4(3H)-one

Выход 56.4%

Растворители

xylene

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was cooled to rt
2. 2
   workup.STIRRINGThe resulting mixture was stirred at rt overnight
3. 3
   Фильтрацияfiltered
4. 4
   Экстракцияthe filtrate was extracted with DCM (20 mL×4)
5. 5
   ПромывкаThe combined organic layers were washed with brine (30 mL×2)
6. 6
   Сушкаdried over anhydrous Na2SO4
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   ДругоеThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Методика

A mixture of N-(3-chloro-4-morpholinophenyl)-3-oxobutanamide (0.59 g, 2.0 mmol), 2-((4-chloronaphthalen-1-yl)oxy)acetamide (0.94 g, 4.0 mmol) and titanium tetraisopropanolate (4.8 mL) in xylene (10 mL) was stirred at 165° C. for 24 h. The mixture was cooled to rt and 60 mL of toluene and 60 mL of saturated NH4Cl aqueous solution were added. The resulting mixture was stirred at rt overnight and filtered and the filtrate was extracted with DCM (20 mL×4). The combined organic layers were washed with brine (30 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (0.56 g, 56%). The compound was characterized by the following spectroscopic data:

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