Réaction #4784

Équation de réaction

methyl 6-bromomethyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate

N-methylpiperazine

→

methyl 6-(4-methylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate

Rendement 23.6%

Solvants

isopropyl alcohol

Conditions de réaction

Traitement

1. 1
   AutreAfter evaporating the solvent
2. 2
   workup.DISSOLUTIONthe residue was dissolved in a mixture of chloroform (50 ml) and water (50 ml)
3. 3
   AutreThe organic layer was separated
4. 4
   Séchagedried over magnesium sulfate
5. 5
   Autreevaporated in vacuo
6. 6
   Lavageeluting with chloroform
7. 7
   workup.ADDITIONThe fractions containing the object compound
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   AutreThe residual crystal was recrystallized from a mixture of diethyl ether and ethanol

Mode opératoire

To a suspension of methyl 6-bromomethyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (1.5 g) in isopropyl alcohol (15 ml) was added N-methylpiperazine (0.88 g) at 70° C. The reaction mixture was stirred for 10 minutes at the same temperature. After evaporating the solvent, the residue was dissolved in a mixture of chloroform (50 ml) and water (50 ml). The organic layer was separated, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to column chromatography on alumina (100 g) eluting with chloroform. The fractions containing the object compound were combined and concentrated under reduced pressure. The residual crystal was recrystallized from a mixture of diethyl ether and ethanol to give methyl 6-(4-methylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (0.37 g).

Source