Reaktion #84499

Reaktionsgleichung

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

acetamide

xylene

NH4Cl

→

title compound

Ausbeute 29.7%

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

Ausbeute 29.7%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then cooled to rt
2. 2
   workup.STIRRINGthe resulting mixture was stirred further at rt overnight
3. 3
   FiltrationThe mixture was then filtered
4. 4
   Extraktionthe filtrate was extracted with DCM (15 mL×3)
5. 5
   WaschenThe combined organic layers were washed with brine (15 mL×2)
6. 6
   Trocknendried over anhydrous Na2SO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:2)

Vorschrift

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:

Quelle