3,4,5-Trimethoxyphenol → 5,7-Dimethyl-2-(3-nitrophenyl)-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazine

HRID 1270306

Reaktionsgleichung

Reaktionsgleichung von HRID 1270306
CC(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([OH:19])[CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16].[CH3:20][C:21]1[N:22]=[C:23]([CH3:44])[N:24]2[C:29]=1[C:28](N1C=NC=N1)=[N:27][C:26]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-:43])=[O:42])[CH:36]=1)=[N:25]2>O1CCCC1>[CH3:20][C:21]1[N:22]=[C:23]([CH3:44])[N:24]2[C:29]=1[C:28]([O:19][C:11]1[CH:12]=[C:13]([O:17][CH3:18])[C:14]([O:15][CH3:16])=[C:9]([O:8][CH3:7])[CH:10]=1)=[N:27][C:26]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-:43])=[O:42])[CH:36]=1)=[N:25]2

Komponenten

5

Edukt 3

HCID 695053,4,5-TrimethoxyphenolHCID 184491105,7-Dimethyl-2-(3-nitrophenyl)-4-(1H-1,2,4-triazol-1-yl)imidazo[5,1-f][1,2,4]triazineHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 184491115,7-Dimethyl-2-(3-nitrophenyl)-4-(3,4,5-trimethoxyphenoxy)imidazo[5,1-f][1,2,4]triazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 175.17 mg (1.04 mmol) of potassium tert-butoxide and 287.53 mg (1.56 mmol) of 3,4,5-trimethoxyphenol in 20 ml of tetrahydrofuran is stirred for 30 min. 350 mg (1.04 mmol) of 5,7-dimethyl-2-(3-nitrophenyl)-4-(1H-1,2,4-triazol-1-yl)imidazo[5,1-f][1,2,4]triazine from example 12A are added thereto and the mixture is heated for 2 h to 70° C. After cooling, the solvent is removed and the residue is taken up and extracted with dichloromethane and 1N sodium hydroxide solution. The organic phase is separated off, dried and the crude product is purified by flash chromatography. (Eluent: dichloromethane/methanol 100:1).

Aufarbeitung

  1. temperaturethe mixture is heated for 2 h to 70° C
  2. temperatureAfter cooling
  3. customthe solvent is removed
  4. extractionextracted with dichloromethane and 1N sodium hydroxide solution
  5. customThe organic phase is separated off
  6. customdried
  7. customthe crude product is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-294f268b96ca4bffaec93c1bc25a8321
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202243B2

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