تفاعل #4776

معادلة التفاعل

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

المذيبات

n-butanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر