Methanol → HCID 66775592, compound

HRID 1645227Notes

Reaction equation

HRID 1645227 reaction equation
[CH3:1][O-:2].[Na+].CO.CS([C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=2)[N:13]2[N:26]=[CH:27][N:28]=[C:12]2[N:11]=1)(=O)=O>O>[CH3:1][O:2][C:10]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=2)[N:13]2[N:26]=[CH:27][N:28]=[C:12]2[N:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 25007188HCID 25007188, compound

Product 1

HCID 66775592HCID 66775592, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

62 mg of a sodium methoxide 28% methanol solution was added to a methanol 3 mL solution of 100 mg of 5-(methylsulfonyl)-7-(5-(trifluoromethyl)pyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidine, followed by stirring at room temperature for 5 minutes. After completion of the reaction, water was added to the reaction liquid, followed by extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1) to obtain 85 mg of the desired product.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-f8a754325fc64a1fa59f2fafdce4d38c
Source dataset
uspto-grants-2012_02
Patent number
US08124760B2

Reaction notes

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