2(1H)-Pyrimidinone, tetrahydro- → HCID 59586732, Verbindung

HRID 218529

Reaktionsgleichung

Reaktionsgleichung von HRID 218529
[NH:1]1[CH2:6][CH2:5][CH2:4][NH:3][C:2]1=[O:7].CC(C)([O-])C.[K+].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[CH:24]([CH3:26])[CH3:25]>CS(C)=O.O>[CH:24]([C:16]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:15]=1[N:1]1[CH2:6][CH2:5][CH2:4][NH:3][C:2]1=[O:7])([CH3:26])[CH3:25]

Komponenten

6

Edukt 3

HCID 746152(1H)-Pyrimidinone, tetrahydro-HCID 23665647Potassium tert-butoxideHCID 59860488HCID 59860488, Verbindung

Produkt 1

HCID 59586732HCID 59586732, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

347 mg (3.47 mmol) of tetrahydropyrimidinone in 21 ml of DMSO are admixed at RT with 584 mg (5.21 mmol) of potassium tert-butoxide, and the mixture is stirred at RT for 45 min. 700 mg (3.82 mmol) of 1-fluoro-2-isopropyl-4-nitrobenzene are added and the mixture is stirred at 60° C. After 18 h, it is cooled and diluted with 250 ml of water. It is extracted three times with ethyl acetate and the combined organic phases are dried over sodium sulfate. After filtration, the solvents are removed under reduced pressure and the residue is purified by chromatography on silica gel (1:5→1:10 cyclohexane/ethyl acetate). This affords 140 mg (14% of theory) of the desired compound.

Aufarbeitung

  1. stirringthe mixture is stirred at 60° C
  2. waitAfter 18 h
  3. temperatureit is cooled
  4. extractionIt is extracted three times with ethyl acetate
  5. dry with materialthe combined organic phases are dried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvents are removed under reduced pressure
  8. customthe residue is purified by chromatography on silica gel (1:5→1:10 cyclohexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8a186f2eb15b422db9d30e34aaf3fc64
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198267B2

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