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Cesium carbonate → [4-(2-Hydroxy-ethyl)-piperazin-1-yl]-[5-(5-nitro-pyrimidin-2-ylamino)-Pyridin-2-yl]methanone
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 5-Nitropyrimidin-2-amine | HCID 76490 | — |
| 反応物 | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| 反応物 | (5-Bromo-pyridin-2-yl)-(4-(2-hydroxy-ethyl)-piperazin-1-yl)-methanone | HCID 58748747 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | [4-(2-Hydroxy-ethyl)-piperazin-1-yl]-[5-(5-nitro-pyrimidin-2-ylamino)-Pyridin-2-yl]methanone | HCID 58748708 | 40% |
反応手順
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.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08030487B2 |
| 出典データセット | uspto-grants-2011_10 |
| ORD ID | ord-34d0626db6e243d694b35cb2bc284c9b |
| 出典メモ | uspto-grants-2011_10 |