Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 178461480 | HCID 178461480 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68430955 | HCID 68430955 | 59.2% |
Reaction Steps
4-Hydroxy-2-(tetrahydro-2H-pyran-2-yl)-5-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-3(2H)-one (250 mg, 0.72 mmol) in N,N-dimethylformamide (2.5 mL) was mixed with methyl iodide (70 μL, 0.76 mmol) and potassium carbonate (104 mg, 0.76 mmol) at room temperature and stirred at 65° C. for 1 hour. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to give the desired product (154 mg, 59% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08440666B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-3406803cb05c4953b1f982e1d91ec19b |
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| Source note | uspto-grants-2013_05 |
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