Triethylamine → 1,3-dimethyl-6-[4-(3-[3-nitrophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

HRID 1085254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1085254
CN1C(N(CCNCCC[C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)CCC2C=CC=CC=2)=CC(=O)N(C)C1=O.[CH3:35][N:36]1[C:41]([N:42]2[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)=[CH:40][C:39](=[O:48])[N:38]([CH3:49])[C:37]1=[O:50].[CH2:51](N(CC)CC)C.O1[CH2:63][CH2:62][O:61]CC1>>[CH3:35][N:36]1[C:41]([N:42]2[CH2:47][CH2:46][N:45]([CH2:51][CH2:63][CH2:62][O:61][C:24]3[CH:23]=[CH:28][CH:27]=[C:26]([N+:29]([O-:31])=[O:30])[CH:25]=3)[CH2:44][CH2:43]2)=[CH:40][C:39](=[O:48])[N:38]([CH3:49])[C:37]1=[O:50]

Komponenten

5

Edukt 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×HCID 200611741,3-dimethyl-6-{N-(2-phenylethyl)-2-[3-(4-nitrophenyl)propylamino]ethylamino)-2,4-(1H,3H)-pyrimidinedione

Produkt 1

HCID 100012161,3-dimethyl-6-[4-(3-[3-nitrophenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

Versuchsvorschrift

In 20 ml of dioxane were dissolved 1.69 g of the above oily compound 39, 1.12 g of 1,3-dimethyl-6-(1-piperazinyl)-2,4(1H,3H)-pyrimidinedione (compound 37) and 1 ml of triethylamine, and the solution was then heated under reflux for 4 hours to perform reaction. After completion of the reaction, insoluble matters were removed from the reaction mixture by filtration, the resulting filtrate was then concentrated. The residue (concentrate) was dissolved in chloroform, and the resulting chloroform solution was then washed with water. Afterward, the water-washed organic layer was dried over anhydrous magnesium sulfate and then treated under reduced pressure to distill off the solvent. Furthermore, the residue was purified through a silica gel column chromatograph (chloroform/methanol=100/1 to 25/1 in terms of volume ratio), and the purified material was then recrystallized from methanol. Afterward, the crystals were collected by filtration, washed and dried in order to obtain 1.35 g of 1,3-dimethyl-6-{4-[3-(3-nitrophenoxy)propyl]piperazin-1-yl}-2,4(1H,3 H)-pyrimidinedione.

Aufarbeitung

  1. temperaturethe solution was then heated
  2. temperatureunder reflux for 4 hours
  3. customreaction
  4. customAfter completion of the reaction, insoluble matters
  5. customwere removed from the reaction mixture by filtration
  6. concentrationthe resulting filtrate was then concentrated
  7. concentrationThe residue (concentrate)
  8. dissolutionwas dissolved in chloroform
  9. washthe resulting chloroform solution was then washed with water
  10. washAfterward, the water-washed organic layer
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. additiontreated under reduced pressure
  13. distillationto distill off the solvent
  14. customFurthermore, the residue was purified through a silica gel column chromatograph (chloroform/methanol=100/1 to 25/1 in terms of volume ratio)
  15. customthe purified material was then recrystallized from methanol
  16. filtrationAfterward, the crystals were collected by filtration
  17. washwashed
  18. customdried in order

Quellen und Nachweise

ORD-Eintrag
ord-6d0e8732b4e7402cb172c9cb062df6e6
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05008267

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