Dibromomethane → [1,3]Oxathiolo[5,4-c]pyridin-6-ylmethanol

HRID 639038Notes

Reaction equation

HRID 639038 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[CH:7][C:6]([OH:9])=[C:5]([SH:10])[CH:4]=1.Br[CH2:12]Br>CN(C=O)C.C(=O)([O-])[O-].[K+].[K+]>[S:10]1[C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[N:8]=[CH:7][C:6]=2[O:9][CH2:12]1

Participants

5

Reactant 2

HCID 3024DibromomethaneHCID 1785197826-(Hydroxymethyl)-4-mercaptopyridin-3-ol

Product 1

HCID 67426109[1,3]Oxathiolo[5,4-c]pyridin-6-ylmethanolYield 70.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of 6-(hydroxymethyl)-4-mercapto-3-pyridinol (500 mg, 3.2 mmol) in anhydrous DMF, potassium carbonate was added. The reaction mixture was stirred for 10 minutes and dibromomethane (0.44 mL, 6.4 mmol) was added. The reaction mixture was stirred at 70° C. for 18 hours under an argon atmosphere. DMF was removed in vacuo and the residue was partitioned between 5% MeOH in dichloromethane and water. The aqueous layer was extracted several times with 5% methanol in dichloromethane. The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. The residue was chromatographed on silica gel eluting with 3-5% methanol in dichloromethane to afford the product as a solid (381 mg, 70%); MS (+ve ion electrospray) m/z 170 (MH+).

Workup

  1. stirringThe reaction mixture was stirred at 70° C. for 18 hours under an argon atmosphere
  2. customDMF was removed in vacuo
  3. customthe residue was partitioned between 5% MeOH in dichloromethane and water
  4. extractionThe aqueous layer was extracted several times with 5% methanol in dichloromethane
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue was chromatographed on silica gel eluting with 3-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-d3c99dfe90e846acbe7550c9e9ec06a6
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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