반응 #84499

반응 방정식

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

acetamide

xylene

NH4Cl

→

title compound

수율 29.7%

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

수율 29.7%

용매

toluene

반응 조건

후처리

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

실험 절차

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:

출처