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

HRID 2238686Notes

Reaction equation

HRID 2238686 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 686876344-(8-Methoxyimidazo[1,2-a]pyridin-3-yl)-2-(methylthio)pyrimidine-5-carbonitrileYield 36.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5f64e0cc755544f195fca58ccc591315
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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