Methyl iodide → 4-(8-Methoxyimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile

HRID 2238686Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2238686
[OH:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([S:19][CH3:20])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI>CS(C)=O.C(Cl)(Cl)Cl>[CH3:21][O:1][C:2]1[C:3]2[N:4]([C:8]([C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([S:19][CH3:20])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68690427HCID 68690427, Verbindung

Produkt 1

HCID 686876344-(8-Methoxyimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrileAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

150 mg of the 4-(8-hydroxyimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile [158-1] was dissolved in 3 mL of dimethylsulfoxide, then 293 mg of potassium carbonate and 40 μL of methyl iodide were added thereto, and stirred at room temperature for 30 minutes. The reaction solution was diluted in 200 mL of chloroform, and washed with water. Then, the organic layer was dried over anhydrous magnesium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in a small amount of a mixed solvent of chloroform and methanol (chloroform:methanol=9:1), and solidified by hexane, to obtain 58 mg of 4-(8-methoxyimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrile [158-2] as a brown solid.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe insolubles were filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in a small amount of a mixed solvent of chloroform and methanol (chloroform:methanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-5f64e0cc755544f195fca58ccc591315
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718801B2

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