Methanol → Methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxybut-2-enoate

HRID 847119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 847119
[OH:1][CH:2]([CH:7]=[CH2:8])[C:3]([O:5][CH3:6])=[O:4].[CH3:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[N:14]=[C:13](S(C)(=O)=O)[N:12]=1.C(=O)([O-])[O-].[K+].[K+].CO>C(C(C)=O)C.C(Cl)(Cl)Cl>[CH3:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[N:14]=[C:13]([O:1][C:2](=[CH:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4])[N:12]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 545123Methyl 2-hydroxybut-3-enoateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Produkt 1

HCID 53952661Methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxybut-2-enoateAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-hydroxybut-3-enoate (0.80g, 6.9mmol), 4,6-dimethoxy-2-methanesulphonylpyrimidine (1.50g, 6.9mmol) and potassium carbonate (1.04g, 7.6mmol) in methyl ethyl ketone (100ml) was refluxed for 12 hours. The reaction mixture was filtered and the filtrate evaporated in vacuo. Flash column chromatography (silica, 1.5% methanol in chloroform) of the residue gave the title compound (1.37g, 78% yield by weight).

Aufarbeitung

  1. temperaturewas refluxed for 12 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-926200faf6b44bfaa25326ff0c79f915
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05139563

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