Dimethyl Sulfate → 6-Bromo-3-methyl[1,3]oxazolo[4,5-b]pyridin-2(3H)-one

HRID 620746Notes

Reaction equation

HRID 620746 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[O:10][C:9](=[O:11])[NH:8][C:5]2=[N:6][CH:7]=1.[Li]N([Si](C)(C)C)[Si](C)(C)[CH3:15].COS(OC)(=O)=O>C1COCC1>[CH3:15][N:8]1[C:5]2=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=[C:4]2[O:10][C:9]1=[O:11]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 136144586-Bromo-3H-oxazolo(4,5-b)pyridin-2-oneHCID 178418261HCID 178418261, compound

Product 1

HCID 159260166-Bromo-3-methyl[1,3]oxazolo[4,5-b]pyridin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 4.7 g of 6-bromo-oxazolo[4,5-b]-pyridin-2(3H)-one (0.022 mole) in 90 ml of THF is added 24 ml of LiN(TMS)2 (0.024 mole) in THF. The homogenous solution is maintained under nitrogen at room temperature for 20 min., 3.03 g (0.024 mole) of dimethylsulfate is added and the reaction mixture allowed to stir overnight. The reaction mixture is then quenched with 20 ml of sat. ammonium chloride and extracted with 3×80 ml ethyl acetate.

Workup

  1. customThe reaction mixture is then quenched with 20 ml of sat. ammonium chloride
  2. extractionextracted with 3×80 ml ethyl acetate

Sources & evidence

ORD record
ord-c0d68a5c256f49c4b5b04fb737e6ea95
Source dataset
uspto-grants-1989_04
Patent number
US04822794

Reaction notes

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