HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1860375Generated: October 30, 2026
Methyl 4-prop-2-ynylcyclohexanecarboxylate → Apadenoson
https://huagongshe.com/reaction/1860375
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl 4-prop-2-ynylcyclohexanecarboxylate | HCID 10749876 | — |
| Reactant | (2s,3s,4r,5r)-5-(6-Amino-2-Iodo-9h-Purin-9-Yl)-N-Ethyl-3,4-Dihydroxytetrahydrofuran-2-Carboxamide | HCID 11697766 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Apadenoson | HCID 9805430 | 24% |
Reaction Steps
To a degassed solution of 25 mg (0.063 mmol) of [(2S,3S,4R,5R)-5-(6-amino-2-iodopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-N-ethylcarboxamide (6.9), 16.9 mg (0.094 mmol) (5.5), and 0.75 mg CuI in 5 mL each of TEA and acetonitrile was added 15 mg of Pd(PPh3)4. The solution was stirred for 24 hours at 70° C. after which time the solution was filtered through celite and chromatographed on silica gel with MeOH—CHCl3 (5:95) to give DWH-146e (24%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06531457B2 |
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| Source dataset | uspto-grants-2003_03 |
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| ORD ID | ord-dca7fde779f344009b704958beb72512 |
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| Source note | uspto-grants-2003_03 |
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