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Water → 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylic acid

HRID 979133
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 979133
[CH3:1][N:2]([C:4]1[CH:22]=[CH:21][C:7]([NH:8][C:9]2[NH:10][C:11](=[O:20])[C:12]([C:15]([O:17]CC)=[O:16])=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:3].[OH-].[Na+].O>C(O)(=O)C>[CH3:3][N:2]([C:4]1[CH:22]=[CH:21][C:7]([NH:8][C:9]2[NH:10][C:11](=[O:20])[C:12]([C:15]([OH:17])=[O:16])=[CH:13][N:14]=2)=[CH:6][CH:5]=1)[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13562809ethyl 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylate

Produkt 1

HCID 135628501,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylic acidAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic Acid
Lösungsmittel

Versuchsvorschrift

Ethyl 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylate (7.5 g) and sodium hydroxide (3.0 g) are added to water (150 ml), and the mixture is refluxed with stirring for 1 hour. After cooling, the reaction mixture is acidified with acetic acid, and the resulting solid is collected by filtration and recrystallized from DMF. The precipitate is collected by filtration and added to water (50 ml), and the mixture is refluxed with stirring for 1 hour. After cooling, the resulting product is collected by filtration and dried at 80° C. under reduced pressure to give 1,6-dihydro-2-[4-(N,N-dimethylamino)anilino]-6-oxo-5-pyrimidinecarboxylic acid (5 g). M.p. 261°-263° C.

Aufarbeitung

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe resulting solid is collected by filtration
  4. customrecrystallized from DMF
  5. filtrationThe precipitate is collected by filtration
  6. additionadded to water (50 ml)
  7. temperaturethe mixture is refluxed
  8. stirringwith stirring for 1 hour
  9. temperatureAfter cooling
  10. filtrationthe resulting product is collected by filtration
  11. customdried at 80° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d1fadec1510643ed9297b5beaaca5b08
Quelldatensatz
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04666915

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