Réaction #84499

Équation de réaction

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

acetamide

xylene

NH4Cl

→

title compound

Rendement 29.7%

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

Rendement 29.7%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   TempératureThe 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
   Extractionthe filtrate was extracted with DCM (15 mL×3)
5. 5
   LavageThe combined organic layers were washed with brine (15 mL×2)
6. 6
   Séchagedried over anhydrous Na2SO4
7. 7
   Concentrationconcentrated in vacuo
8. 8
   AutreThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:2)

Mode opératoire

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:

Source