Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Sulfoxonium, trimethyl-, iodide (1:1) | HCID 74498 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | Ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)-methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexylidene)acetate | HCID 66733552 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Sodium Chloride | HCID 5234 | — |
| Product | HCID 66738525 | HCID 66738525 | — |
Reaction Steps
To 50 mL roundbottom flask containing trimethylsulfoxonium iodide (3.57 mmol, 785 mg) in DMSO (8 mL) was added potassium tert-butoxide (3.57 mmol, 401 mg). This suspension was allowed to stir at room temperature for 3 hours. After 3 hours, ethyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexylidene)acetate (1.78 mmol, 1.00 g) was added in 2 mL DMSO. The resulting solution was stirred at room temperature for 18 hours. After 18 hours, the reaction was diluted with saturated NaCl(aq) (30 mL). The pH was adjusted to ˜7 with saturated NH4Cl(aq) and extracted with DCM (50 mL) 4 times. The combined organics are dried over Na2SO4 and reduced in vacuo. The resulting residue was purified via flash chromatography to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08591943B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-db3e55cb25ef4a0098d1604ed293ab75 |
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| Source note | uspto-grants-2013_11 |
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