Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Trimethylsilylacetylene | HCID 66111 | — |
| Edukt | Tetramethylammonium fluoride | HCID 67803 | — |
| Edukt | HCID 22249760 | HCID 22249760 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Lösungsmittel | Triethylamine | HCID 8471 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | HCID 86595762 | HCID 86595762 | 48,7% |
Reaktionsschritte
A solution of 8-(1-ethylpropyl)-3-iodo-2,5-dimethyl-7,8-dihydro-6H-pyrazolo[1,5-a]pyrrolo[3,2-e]pyrimidine (2.0 g, 5.29 mmol), trimethylsilylacetylene (0.8 mL, 5.82 mmol), Cl2Pd(PPh3)2 (0.19 g, 0.26 mmol) and copper(I) iodide (50 mg, 0.26 mmol) in triethylamine (20 mL) was stirred at room temperature for two hours. The solution was filtered through Celite, and the filtrate was evaporated. Tetramethylammonium fluoride (1.0 M tetrahydrofuran solution 6.3 mL, 6.3 mmol) was added to a solution of the residue in tetrahydrofuran (20 mL) at room temperature, followed by stirring for 10 minutes. Water was added thereto, and the mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10-20% ethyl acetate/hexane), to give the title compound (727 mg) as pale brown crystals.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patentnummer | US06927221B2 |
|---|
| Quelldatensatz | uspto-grants-2005_08 |
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| ORD ID | ord-19220f35d51b456db0176c70c05bcd77 |
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| Quellennotiz | uspto-grants-2005_08 |
|---|