Dimethyl Sulfate → Acetate hexane

HRID 2393334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393334
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:4]([O:14][C:15]2[CH:19]=[CH:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:16]=2)[N:3]=1.[H-].[Na+].C(CNC[CH:33]=[O:34])=O.[CH3:35]OS(OC)(=O)=O>CN(C)C=O>[C:10]([O-:12])(=[O:11])[CH3:9].[CH3:24][CH2:25][CH2:20][CH2:21][CH2:22][CH3:23].[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9](=[CH:35][O:34][CH3:33])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([O:14][C:15]2[CH:19]=[CH:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:16]=2)[N:3]=1

Komponenten

7

Edukt 4

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 18975605HCID 18975605, VerbindungHCID 202686642,2'-Azanediyldiacetaldehyde

Produkt 2

HCID 22139250Acetate hexaneHCID 67655269HCID 67655269, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The intermediate methyl 2-[2,4-dimethyl-6-(1-phenyl-1H-pyrazol-3-yloxy)-pyrimidin-5-yl]-acetate (6.8 g, 20 mmol), NaH (0.8 g of a 80% suspension in oil, 25 mmol) and N,N-diformylmethylamine (5 ml) in dimethylformamide (40 ml) is stirred at 45° C. for two hours. Dimethylsulfate (2.4 ml, 25 mmol) is added at room temperature and stirring is continued for additional two hours. Dilution with ether, washing with brine, drying and chromatography on silicagel (eluant: ethyl, acetate/hexane 1:1) gives methyl 2-[2,4-dimethyl-6-(1-phenyl-1H-pyrazol-3-yloxy)-pyrimidin-5-yl]-3-methoxyacrylate as a colorless oil.

Aufarbeitung

  1. washDilution with ether, washing with brine
  2. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-e857cfefe4554d14a3e75cbf65ae5c4a
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807863

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