Dimethyl Sulfate → HCID 67654223, Verbindung

HRID 2393337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2393337
[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]([CH2:20][C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])[N:16]=2)[N:3]=1.[H-].[Na+].C(CNC[CH:36]=[O:37])=O.[CH3:38]OS(OC)(=O)=O>CN(C)C=O>[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9](=[CH:38][O:37][CH3:36])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([O:14][C:15]2[CH:19]=[CH:18][N:17]([CH2:20][C:21]3[C:22]([Cl:28])=[CH:23][CH:24]=[CH:25][C:26]=3[Cl:27])[N:16]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 18975622HCID 18975622, VerbindungHCID 202686642,2'-Azanediyldiacetaldehyde

Produkt 1

HCID 67654223HCID 67654223, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

The intermediate methyl 2-[2,4-dimethyl-6-(1-(2,6-dichlorobenzyl)-1H-pyrazol-3-yloxy)-pyrimidin-5-yl]-acetate (9,6 g, 23 mmol) is dissolved in dimethylformamide (20 ml) and added at +30° C. to a suspension of NaH (1.3 g, of a 80% suspension in oil, 46 mmol) and N,N-diformylmethylamine (10 ml) in dimethylformamide (40 ml). The mixture is stirred for 2 hours at +45° C. Dimethylsulfate (2,4 ml, 25 mmol) is added at room temperature with cooling and stirring is continued for additional two hours. Dilution with ether, washing with brine, drying and chromatography on silicagel (eluant:ethyl acetate/hexane 3:1) gives methyl 2-[2,4-dimethyl-6-(1-(2,6-dichlorobenzyl)-1H-pyrazol-3-yloxy)-pyrimidin-5-yl]-3-methoxyacrylate as a colorless oil (4.8 g).

Aufarbeitung

  1. temperaturewith cooling
  2. stirringstirring
  3. waitis continued for additional two hours
  4. washDilution with ether, washing with brine
  5. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-e5c050b72b1d4ead92fe495ed094dc2a
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05807863

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