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

HRID 1607561Notes

Reaction equation

HRID 1607561 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. The ethyl acetate is then washed with 3×30 ml sat. ammonium chloride, dried over sodium sulfate and concentrated to obtain off white product which is used directly in the next step.

Workup

  1. customThe reaction mixture is then quenched with 20 ml of sat. ammonium chloride
  2. extractionextracted with 3×80 ml ethyl acetate
  3. washThe ethyl acetate is then washed with 3×30 ml sat. ammonium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto obtain off white product which

Sources & evidence

ORD record
ord-5206bae8843e406692ffb49fca2e39ce
Source dataset
uspto-grants-1989_09
Patent number
US04866074

Reaction notes

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