Water → 2-[(3,5-Dimethyl-4-methoxy-2-pyridyl)methylthio]-imidazo[4,5-b]pyridine

HRID 1638592Notes

Reaction equation

HRID 1638592 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[C:5]([N:10]=1)=[N:6][CH:7]=[CH:8][CH:9]=2.[H-].[Na+].Cl.Cl[CH2:15][C:16]1[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][N:17]=1.O>CN(C)C=O>[CH3:22][C:21]1[C:16]([CH2:15][S:1][C:2]2[NH:3][C:4]3[C:5]([N:10]=2)=[N:6][CH:7]=[CH:8][CH:9]=3)=[N:17][CH:18]=[C:19]([CH3:25])[C:20]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochlorideHCID 178527819HCID 178527819, compound

Product 1

HCID 137682532-[(3,5-Dimethyl-4-methoxy-2-pyridyl)methylthio]-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 Grams of 2-mercaptoimidazo[4,5-b]pyridine was dissolved in 50 ml of dimethylformamide, to this solution was added, under ice-cooled condition, 0.88 g of 60% sodium hydride (in oil), and the mixture was stirred at the same temperature for 30 minutes. Then, to this reaction mixture was added 2.2 g of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride and the whole mixture was heated at 70° to 80° C. under stirring condition for 3 hours. After the reaction was completed, dimethylformamide was removed by evaporation, and to the residue thus obtained was added water, and then extracted with chloroform. The chloroform extract was washed with water, and dried with anhydrous magnesium sulfate. Chloroform was removed by evaporation, then the residue thus obtained was recrystallized from ethanol to obtain 1.3 g of 2-[(3,5-dimethyl-4-methoxy-2-pyridyl)methylthio]imidazo[4,5-b]pyridine in the form of white powdery crystals. Melting point: 186°-188° C.

Workup

  1. additionwas added, under ice-
  2. temperaturethe whole mixture was heated at 70° to 80° C.
  3. stirringunder stirring condition for 3 hours
  4. customdimethylformamide was removed by evaporation
  5. customto the residue thus obtained
  6. extractionextracted with chloroform
  7. extractionThe chloroform extract
  8. washwas washed with water
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customChloroform was removed by evaporation
  11. customthe residue thus obtained
  12. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-dc57bffc761d4756a005f6886ebb5c43
Source dataset
uspto-grants-1989_11
Patent number
US04880815

Reaction notes

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