Potassium Carbonate → HCID 68690458, compound

HRID 2238688Notes

Reaction equation

HRID 2238688 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(=O)([O-])[O-].[K+].[K+].CC1C=CC(S(O[CH2:38][F:39])(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:39][CH2:38][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 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 13862289Fluoromethyl 4-methylbenzenesulfonateHCID 68690427HCID 68690427, compound

Product 1

HCID 68690458HCID 68690458, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

100 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 N,N-dimethylformamide, 146 mg of potassium carbonate and 216 mg of fluoromethyl 4-methylbenzenesulfonate (synthesized according to a method disclosed in page 555 to 566 in J. Labelled Compd. Radio pharm. 2003, 46) were added, and stirred at 80° C. for 5 hours. After cooling the reaction mixture back to room temperature, a saturated aqueous solution of sodium hydrogen carbonate was added, and was extracted with a mixture solvent of chloroform and methanol (chloroform:methanol=9:1). The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in a small amount of a mixture solvent of chloroform and methanol (chloroform:methanol=9:1), and solidified by adding diethyl ether, to obtain 44.1 mg of 4-[8-(fluoromethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(methylthio)pyrimidine-5-carbonitrile [160-1] as a brown solid.

Workup

  1. addition2003, 46) were added
  2. temperatureAfter cooling the reaction mixture back to room temperature
  3. extractionwas extracted with a mixture solvent of chloroform and methanol (chloroform:methanol=9:1)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in a small amount of a mixture solvent of chloroform and methanol (chloroform:methanol=9:1)
  9. additionby adding diethyl ether

Sources & evidence

ORD record
ord-e1536c965c4648c3b8ebd907a0bc2262
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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