反応 #4776

反応方程式

2-(4-methylpiperazin-1-ylcarbonyl)-1-(3-nitrophenyl)-1-buten-3-one

benzamidine hydrochloride

triethylamine

→

6-methyl-5-(4-methylpiperazin-1-ylcarbonyl)-4-(3-nitrophenyl)-2-phenylpyrimidine

溶媒

n-butanol

反応条件

後処理

1. 1
   温度was refluxed for 2 hours
2. 2
   その他After evaporating the solvent
3. 3
   workup.DISSOLUTIONthe residue was dissolved in a suspension of water (200 ml) and chloroform (200 ml)
4. 4
   洗浄The separated organic layer was washed with saturated aqueous sodium chloride
5. 5
   乾燥dried over magnesium sulfate
6. 6
   workup.ADDITIONTo this solution was added activated manganese dioxide (120 g)
7. 7
   温度the mixture was refluxed for 1 hour
8. 8
   ろ過manganese dioxide was filtered off
9. 9
   その他The filtrate was evaporated in vacuo
10. 10
    洗浄eluting with chloroform
11. 11
    workup.ADDITIONThe fractions containing the object compound
12. 12
    濃縮concentrated under reduced pressure
13. 13
    その他The crystals were recrystallized from diethyl ether

実験手順

A mixture of 2-(4-methylpiperazin-1-ylcarbonyl)-1-(3-nitrophenyl)-1-buten-3-one (20 g), benzamidine hydrochloride (9.9 g) and triethylamine (11.4 ml) in n-butanol (200 ml) was refluxed for 2 hours. After evaporating the solvent, the residue was dissolved in a suspension of water (200 ml) and chloroform (200 ml). The separated organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. To this solution was added activated manganese dioxide (120 g) and the mixture was refluxed for 1 hour with stirring vigorously. After cooling to a room temperature, manganese dioxide was filtered off. The filtrate was evaporated in vacuo, and the residue was subjected to column chromatography on alumina (200 g) eluting with chloroform. The fractions containing the object compound were combined and concentrated under reduced pressure. The crystals were recrystallized from diethyl ether to give 6-methyl-5-(4-methylpiperazin-1-ylcarbonyl)-4-(3-nitrophenyl)-2-phenylpyrimidine.

出典