HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 527988Generated: November 1, 2026
18-Crown-6 → tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate
https://huagongshe.com/reaction/527988
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | Tert-butyl 4-((4-amino-6-chloropyrimidin-5-yl)ethynyl)piperidine-1-carboxylate | HCID 90418839 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)piperidine-1-carboxylate | HCID 90418107 | — |
Reaction Steps
To a solution of Example 1B (250 mg, 0.74 mmol), in toluene (5 mL), was added potassium tert-butoxide (249 mg, 2.22 mmol) followed by 18-crown-6 (15 mg, 0.057 mmol) and the mixture was heated under nitrogen at 65° C. for 12 hours. The mixture was cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, concentrated and purified by column chromatography (silica gel, 40% ethyl acetate in hexane) to afford the title compound. LCMS: 337.1 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09346813B2 |
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| Source dataset | uspto-grants-2016_05 |
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| ORD ID | ord-7e65c9b42da0409e8ac89b9dd68e4146 |
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| Source note | uspto-grants-2016_05 |
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