Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | Chlorotrimethylsilane | HCID 6397 | — |
| Reactant | HCID 22130117 | HCID 22130117 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 22130584 | HCID 22130584 | 34.2% |
Reaction Steps
To a solution of 83 mg of potassium iodide in acetonitrile was added 64 μl of trimethylsilyl chloride under ice-cooling and stirring. The mixture was allowed to warm up, and after 10 minutes, 150 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(2-methoxypyridin-5-ylmethyl)-4-isopropyl-1H-imidazole was added, and the mixture was stirred with heating at 60° C. After 1 hour, the solution was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, extracted with ethyl acetate, the extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate: methanol=10:1) to give 50 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-1-(6-oxo-1,6-dihydro-pyridin-3-yl)methyl-4-isopropyl-1H-imidazole (115a) (yield 34%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06147097 |
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| Source dataset | uspto-grants-2000_11 |
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| ORD ID | ord-679c693607ce4ea48f886321e8e6606b |
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| Source note | uspto-grants-2000_11 |
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