Reaction #4776

Reaction equation

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

Solvents

n-butanol

Conditions

Workup

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

Procedure

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.

Source