Water → FK 664

HRID 65152

Reaktionsgleichung

Reaktionsgleichung von HRID 65152
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:16][C:15](=[O:17])[N:14]([CH3:18])[C:13](=[N:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:29][C:30](C)([O-])C.[K+].C(I)C.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH2:29][CH3:30])[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[N:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6340Iodoethane2×HCID 23665647Potassium tert-butoxide2×HCID 178418505HCID 178418505, Verbindung

Produkt 1

HCID 146868FK 664Ausbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (2.73 g) and potassium tert-butoxide (1.0 g) in dimethylformamide (27 ml) was added ethyl iodide (1.2 ml) and mixture was stirred for 3 hours. Then another potassium tert-butoxide (1.1 g) and ethyl iodide (0.57 ml) were added. The mixture was stirred for more 2 hours and poured into water. The precipitate was collected by filtration and added to 1N hydrochloric acid (15 ml). The mixture was refluxed for 5 hours. After being cooled, the reaction mixture was adjusted to pH 8.5 with aqueous sodium hydroxide. The precipitate was collected by filtration and added to diisopropyl ether (50 ml). The resultant mixture was filtered and the filtrate was evaporated in vacuo. The residue was recrystallized from a mixture of ethanol and water (3:1) to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-1-ethyl-3-methyl-4-(2,4,6-tri-methylphenylimino)-2(1H)-pyrimidinone (1.6 g). mp 116° -118° C.

Aufarbeitung

  1. stirringThe mixture was stirred for more 2 hours
  2. filtrationThe precipitate was collected by filtration
  3. additionadded to 1N hydrochloric acid (15 ml)
  4. temperatureThe mixture was refluxed for 5 hours
  5. temperatureAfter being cooled
  6. filtrationThe precipitate was collected by filtration
  7. additionadded to diisopropyl ether (50 ml)
  8. filtrationThe resultant mixture was filtered
  9. customthe filtrate was evaporated in vacuo
  10. customThe residue was recrystallized from a mixture of ethanol and water (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-9a47148866324999a28a71774bb8d9ad
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612376

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