Dimethyl Sulfate → 2-Methoxypyrazolo[1,5-a]pyridine

HRID 436804Notes

Reaction equation

HRID 436804 reaction equation
[Na].[OH:2][C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.S(OC)(O[CH3:16])(=O)=O>CO>[CH3:16][O:2][C:3]1[CH:11]=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 5360545SodiumHCID 178515341HCID 178515341, compound

Product 1

HCID 122844272-Methoxypyrazolo[1,5-a]pyridineYield 50.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium (92 mg) was dissolved in 5 ml of absolute methyl alcohol with moderate cooling. To this solution 2-hydroxypyrazolo[1,5-a]pyridine (500 mg) was added and then dimethyl sulfate (500 mg) was added. The mixture was stirred for 30 min. at room temperature and refluxed for 8 hr. The reaction mixture was concentrated to remove methyl alcohol, and water was added to the residue. The solution was extracted with n-hexane, and the n-hexane solution was dried over sodium sulfate. The dried n-hexane solution was concentrated and the residue was distilled to give 280 mg of oily product under reduced pressure.

Workup

  1. temperaturerefluxed for 8 hr
  2. concentrationThe reaction mixture was concentrated
  3. customto remove methyl alcohol, and water
  4. additionwas added to the residue
  5. extractionThe solution was extracted with n-hexane
  6. dry with materialthe n-hexane solution was dried over sodium sulfate
  7. concentrationThe dried n-hexane solution was concentrated
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-f69818a69ece405a9de8fcb5e92ee636
Source dataset
uspto-grants-1977_06
Patent number
US04028370

Reaction notes

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