HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Cesium carbonate → [4-(2-Hydroxy-ethyl)-piperazin-1-yl]-[5-(5-nitro-pyrimidin-2-ylamino)-Pyridin-2-yl]methanone
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | 5-Nitropyrimidin-2-amine | HCID 76490 | — |
| Edukt | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Edukt | (5-Bromo-pyridin-2-yl)-(4-(2-hydroxy-ethyl)-piperazin-1-yl)-methanone | HCID 58748747 | — |
| Katalysator | palladium(II) acetate | HCID 167845 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | [4-(2-Hydroxy-ethyl)-piperazin-1-yl]-[5-(5-nitro-pyrimidin-2-ylamino)-Pyridin-2-yl]methanone | HCID 58748708 | 40% |
Reaktionsschritte
A mixture of 5-nitro-pyrimidin-2-ylamine (0.85 g, 6.1 mmol), intermediate 46 (Example 95) (2.5 g, 8.0 mmol), Pd(OAc)2 (0.40 g, 0.44 mmol), Xantphos (0.5 g, 0.86 mmol) and cesium carbonate (4.0 g, 12 mmol) was suspended in dioxane (30 mL) and heated at reflux under the argon atmosphere for 18 h. The mixture was allowed to cool to room temperature, filtered and washed with DCM. The filtrate was concentrated and the crude product purified by flash chromatography on silica gel (5% MeOH/DCM to 15% MeOH/DCM) to afford the title compound (0.90 g, 40%) as a yellow solid.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08030487B2 |
| Quelldatensatz | uspto-grants-2011_10 |
| ORD ID | ord-34d0626db6e243d694b35cb2bc284c9b |
| Quellennotiz | uspto-grants-2011_10 |