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Triethylamine → 1,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl]-piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione

HRID 1196717
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1196717
C1(C2OC3C=C(OCCBr)C=CC=3C(=O)C=2)C=CC=CC=1.CN1C(N2CCNCC2)=CC(=O)N(C)C1=O.C(N(CC)CC)C.C(O)(=O)C(O)=O.[CH3:51][N:52]1[C:57]([N:58]2[CH2:63][CH2:62][N:61]([CH2:64][CH2:65][O:66][C:67]3[CH:83]=[CH:82][C:70]4[C:71](=[O:81])[CH:72]=[C:73]([C:75]5[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=5)[O:74][C:69]=4[CH:68]=3)[CH2:60][CH2:59]2)=[CH:56][C:55](=[O:84])[N:54]([CH3:85])[C:53]1=[O:86]>CN(C)C=O>[CH3:51][N:52]1[C:57]([N:58]2[CH2:59][CH2:60][N:61]([CH2:64][CH2:65][O:66][C:67]3[CH:83]=[CH:82][C:70]4[C:71](=[O:81])[CH:72]=[C:73]([C:75]5[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=5)[O:74][C:69]=4[CH:68]=3)[CH2:62][CH2:63]2)=[CH:56][C:55](=[O:84])[N:54]([CH3:85])[C:53]1=[O:86]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×HCID 198987461,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl]piperazine-1-yl)-2,4-(1H,3H)-pyrimidinedione oxalateHCID 198987572-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl bromide2×

Produkt 1

HCID 19898747
1,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl]-piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione
Ausbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 1.5 ml of N,N-dimethylformamide, there were reacted 0.31 g of the previously obtained 2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl bromide (Compound 9), 0.2 g of 1,3-dimethyl-6-(piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (Compound 3) and 0.4 ml of triethylamine at 100° C. for 1 hour. The resultant reaction solution was poured into ice water and then extracted with chloroform. The resultant chloroform layer was then washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Afterward, the resultant residue was recrystallized from ethanol and hexane to obtain 0.30 g (yield 68%) of 1,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl]-piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (the nonoxalate of Compound 10).

Aufarbeitung

  1. customThe resultant reaction solution
  2. extractionextracted with chloroform
  3. washThe resultant chloroform layer was then washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customAfterward, the resultant residue was recrystallized from ethanol and hexane

Quellen und Nachweise

ORD-Eintrag
ord-229b00d8eace477e849c1f2f1b21db16
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05114941

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