N-Iodosuccinimide → 5-(4-Ethylphenyl)-6-iodofuro[2,3-d]pyrimidin-4(3H)-one

HRID 2189070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189070
[I:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:25]3[C:24](=[O:26])[NH:23][CH:22]=[N:21][C:20]=3[O:19][CH:18]=2)=[CH:13][CH:12]=1)[CH3:10]>C(#N)C.ClC(Cl)(Cl)Cl>[CH2:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:25]3[C:24](=[O:26])[NH:23][CH:22]=[N:21][C:20]=3[O:19][C:18]=2[I:1])=[CH:15][CH:16]=1)[CH3:10]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 582801005-(4-Ethylphenyl)furo[2,3-d]pyrimidin-4(3H)-one

Produkt 1

HCID 582801285-(4-Ethylphenyl)-6-iodofuro[2,3-d]pyrimidin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18669661Acetonitrile tetrachloromethaneLösungsmittel

Versuchsvorschrift

Add 7.0 g (31.3 mmol) of N-iodosuccinimide to a solution of 5.0 g (20.9 mmol) of 5-(4-ethylphenyl)furo[2,3-d]pyrimidin-4(3H)-one in 250 ml of acetonitrile/tetrachloromethane (1:1). Stir the resulting suspension under reflux for two hours. After cooling to room temperature, concentrate the reaction mixture under reduced pressure. Stir the residue in ethyl acetate and filter. Add water to the filtrate. After removal of the organic phase, extract the aqueous phase repeatedly with ethyl acetate. Concentrate the combined organic phases under reduced pressure. Take up the residue in ethyl acetate and chromatograph it on silica gel (eluent: cyclohexane/ethyl acetate 1:1→1:2). Stir the resulting solid in diethyl ether/n-pentane and filter. 1.4 g (85% purity, 16% of theory) of the target compound are obtained.

Aufarbeitung

  1. temperatureunder reflux for two hours
  2. concentrationconcentrate the reaction mixture under reduced pressure
  3. stirringStir the residue in ethyl acetate
  4. filtrationfilter
  5. customAfter removal of the organic phase
  6. extractionextract the aqueous phase repeatedly with ethyl acetate
  7. concentrationConcentrate the combined organic phases under reduced pressure
  8. stirringStir the resulting solid in diethyl ether/n-pentane
  9. filtrationfilter
  10. custom1.4 g (85% purity, 16% of theory) of the target compound are obtained

Quellen und Nachweise

ORD-Eintrag
ord-85a78d902a304e239b90b5a591cb5f0a
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324222B2

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