Hydrochloric Acid → 3-(4-chloro-6-fluoro-2-hydroxy-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 277437

Reaktionsgleichung

Reaktionsgleichung von HRID 277437
N(OC(C)(C)C)=[O:2].N[C:9]1[C:14]([O:15][CH3:16])=[C:13]([Cl:17])[CH:12]=[C:11]([F:18])[C:10]=1[N:19]1[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]1=[O:31].Cl>S([O-])([O-])(=O)=O.[Cu+2].[Cu-]=O.O.[N+]([O-])([O-])=O.[Cu+2].O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(#N)C>[Cl:17][C:13]1[CH:12]=[C:11]([F:18])[C:10]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])=[C:9]([OH:2])[C:14]=1[O:15][CH3:16]

Komponenten

8

Edukt 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 183145373-(2-Amino-4-chloro-6fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)pyrimidinedione

Produkt 1

HCID 572512883-(4-chloro-6-fluoro-2-hydroxy-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24462Copper SulfateKatalysatorHCID 167780Copper(II) nitrate hemipentahydrateKatalysatorHCID 178419072HCID 178419072, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

An acetonitrile (10 ml) solution of copper (II) sulfate (0.52 g, 3.26 mmol), copper (I) oxide (0.47 g, 3.26 mmol) and copper (II) nitrate hemipentahydrate (0.76 g, 3.26 mmol) was stirred at −30° C., and added with tert-butyl nitrite (0.41 g, 3.97 mmol) and then an acetonitrile (3 ml) solution of 3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.94 g, 2.56 mmol). After stirred for 16 hr (−30° C. to room temperature), the mixture was poured into cold 5% hydrochloric acid (30 ml) and then extracted with ethyl acetate (20 ml×3). The organic phase was washed with brine and dried over Na2SO4. Preparative TLC was used for purification (silica gel plates, 2000 microns, ether). Yield: 0.16 g, 0.44 mmol.

Aufarbeitung

  1. extractionextracted with ethyl acetate (20 ml×3)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customPreparative TLC was used for purification (silica gel plates, 2000 microns, ether)

Quellen und Nachweise

ORD-Eintrag
ord-1957e37683444cdcbe5a1cf20c9e049f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355799B1

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