反応 #84569

反応方程式

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

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

toluene

NH4Cl

→

title compound

収率 56.4%

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

収率 56.4%

溶媒

xylene

反応条件

後処理

1. 1
   温度The mixture was cooled to rt
2. 2
   workup.STIRRINGThe resulting mixture was stirred at rt overnight
3. 3
   ろ過filtered
4. 4
   抽出the filtrate was extracted with DCM (20 mL×4)
5. 5
   洗浄The combined organic layers were washed with brine (30 mL×2)
6. 6
   乾燥dried over anhydrous Na2SO4
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

実験手順

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:

出典