Reacción #4776

Ecuación de reacción

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

Disolventes

n-butanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente