Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Hydantoin | HCID 10006 | — |
| Reactant | Tert-butyl 5-(benzylthio)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate | HCID 86714600 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 178518497 | HCID 178518497 | 83.9% |
Reaction Steps
Hydantoin (67 mg, 0.67 mmol) and piperidine (66 μL, 0.67 mmol) were added to tert-butyl 5-(benzylthio)-3-formylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (95 mg, 0.22 mmol) dissolved in ethanol (1.1 mL). The reaction was heated at 80° C. After 15 h, the reaction was cooled to r.t., diluted with water (5 mL), and the precipitate was collected and washed with 1:1 ethanol:water (10 mL) and then ethanol (3 mL). The bright yellow solid was dried in vacuo to give (Z)-5-((5-(benzylthio)-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (75 mg, 66%). LCMS (ES): >95% pure, m/z 507 [M+1]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09303033B2 |
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| Source dataset | uspto-grants-2016_04 |
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| ORD ID | ord-6b13679da5fc48c9b9a9539d76fcd926 |
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| Source note | uspto-grants-2016_04 |
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