Water → 6-(3,4-Dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenoxy)pyrimidine

HRID 4341

Reaktionsgleichung

Reaktionsgleichung von HRID 4341
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[H-].[Na+].Cl[C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[N:17]=[C:16]([CH3:30])[N:15]=1.O>CN(C)C=O>[CH3:29][O:28][C:22]1[CH:21]=[C:20]([C:18]2[N:17]=[C:16]([CH3:30])[N:15]=[C:14]([O:10][C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])[CH:19]=2)[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

Komponenten

6

Edukt 4

HCID 962WaterHCID 106982,4,6-TrimethylphenolHCID 24758Sodium hydrideHCID 201522714-Chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine

Produkt 1

HCID 201522566-(3,4-Dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenoxy)pyrimidineAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,4,6-trimethylphenol (1.03 g) in N,N-dimethylformamide (20 ml) was added sodium hydride (60% in oil, 0.30 g), and stirred at ambient temperature for 5 minutes. To the solution was added 4-chloro-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (2.0 g), and the mixture was stirred at ambient temperature for 18 hours. The solution was poured into water (300 ml), and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel eluting with chloroform to give 6-(3,4-dimethoxyphenyl)-2-methyl-4-(2,4,6-trimethylphenoxy)pyrimidine (1.96 g).

Aufarbeitung

  1. stirringthe mixture was stirred at ambient temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-8c0e664d28f44521b67fd86394cabfa0
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725600

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