반응 #4776

반응 방정식

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

용매

n-butanol

반응 조건

후처리

1. 1
   온도was refluxed for 2 hours
2. 2
   기타After evaporating the solvent
3. 3
   workup.DISSOLUTIONthe residue was dissolved in a suspension of water (200 ml) and chloroform (200 ml)
4. 4
   세척The separated organic layer was washed with saturated aqueous sodium chloride
5. 5
   건조dried over magnesium sulfate
6. 6
   workup.ADDITIONTo this solution was added activated manganese dioxide (120 g)
7. 7
   온도the mixture was refluxed for 1 hour
8. 8
   여과manganese dioxide was filtered off
9. 9
   기타The filtrate was evaporated in vacuo
10. 10
    세척eluting with chloroform
11. 11
    workup.ADDITIONThe fractions containing the object compound
12. 12
    농축concentrated under reduced pressure
13. 13
    기타The crystals were recrystallized from diethyl ether

실험 절차

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.

출처