Butyl 4-aminobenzoate → Ethyl 1,6-dihydro-2-(4-butoxycarbonylanilino)-6-oxo-5-pyrimidinecarboxylate

HRID 979121

Reaktionsgleichung

Reaktionsgleichung von HRID 979121
CS[C:3]1[NH:4][C:5](=[O:14])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:8]=1.[CH2:15]([O:19][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH3:18]>C(O)C>[CH2:15]([O:19][C:20]([C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:3]2[NH:4][C:5](=[O:14])[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][N:8]=2)=[CH:25][CH:26]=1)=[O:28])[CH2:16][CH2:17][CH3:18]

Komponenten

4

Edukt 2

HCID 2482Butyl 4-aminobenzoateHCID 239049Ethyl 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarboxylate

Produkt 1

HCID 13562812Ethyl 1,6-dihydro-2-(4-butoxycarbonylanilino)-6-oxo-5-pyrimidinecarboxylateAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 1,6-dihydro-2-methylthio-6-oxo-5-pyrimidinecarboxylate (10 g) and butyl -4-aminobenzoate (10.8 g) are added to ethanol (100 ml), and the mixture is refluxed with stirring for 48 hours. After cooling, the precipitate is collected by filtration and recrystallized from a mixture of DMF and water to give ethyl 1,6-dihydro-2-(4-butoxycarbonylanilino)-6-oxo-5-pyrimidinecarboxylate (7.0 g). M.p. 281°-283° C.

Aufarbeitung

  1. temperaturethe mixture is refluxed
  2. temperatureAfter cooling
  3. filtrationthe precipitate is collected by filtration
  4. customrecrystallized from a mixture of DMF and water

Quellen und Nachweise

ORD-Eintrag
ord-af91b5896fc74264967fab2191b6c057
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04666915

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