Реакция #84499

Уравнение реакции

N-(3-fluoro-4-((3-(tetrahydrofuran-2-yl)propyl)amino)phenyl)-3-oxobutanamide

acetamide

xylene

NH4Cl

→

title compound

Выход 29.7%

3-(3-fluoro-4-((3-(tetrahydrofuran-2-yl)propyl)amino)phenyl)-2,6-dimethyl-pyrimidin-4(3H)-one

Выход 29.7%

Растворители

toluene

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was then cooled to rt
2. 2
   workup.STIRRINGthe resulting mixture was stirred further at rt overnight
3. 3
   ФильтрацияThe mixture was then filtered
4. 4
   Экстракцияthe filtrate was extracted with DCM (15 mL×3)
5. 5
   ПромывкаThe combined organic layers were washed with brine (15 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)=1:2)

Методика

A mixture of N-(3-fluoro-4-((3-(tetrahydrofuran-2-yl)propyl)amino)phenyl)-3-oxobutanamide (250 mg, 0.78 mmol), acetamide (92 mg, 1.56 mmol), titanium tetraisopropanolate (1.9 mL) and xylene (10 mL) was stirred at 165° C. for 24 h. The mixture was then cooled to rt. 60 mL of toluene and 60 mL of saturated NH4Cl aqueous solution were added and the resulting mixture was stirred further at rt overnight. The mixture was then filtered and the filtrate was extracted with DCM (15 mL×3). The combined organic layers were washed with brine (15 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:2) to give the title compound as a yellow solid (80 mg, 29%). The compound was characterized by the following spectroscopic data:

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