Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phenol | HCID 996 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2,2,6,6-Tetramethyl-3,5-heptanedione | HCID 70700 | — |
| Reactant | HCID 90408799 | HCID 90408799 | — |
| Catalyst | Cuprous chloride | HCID 62652 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 90408710 | HCID 90408710 | 84.4% |
Reaction Steps
2-(4-Bromobenzyl)-7,8-dihydro-5,7,7-trimethyl-[2H]-imidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-one (118 g, 304 mmol) is added into a suspension of phenol (57 g, 606 mmol) and cesium carbonate (200 g, 614 mmol) in NMP (900 mL), followed by 2,2,6,6-tetramethylheptane-3,5-dione (7 mL, 33.5 mmol) and CuCl (15 g, 152 mmol). The reaction mixture is heated at 120° C. under argon atmosphere for 10 h. After the completion of the reaction, the mixture is diluted with water (4 L), and then extracted with ethyl acetate. The combined organic phase is evaporated to dryness. The obtained crude product is purified by silica gel column chromatography to give 103 g of product (yield: 84%). MS (ESI) m/z 402.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09073936B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-6d55e7b6a6ad4a5fa2db0b9c646a6988 |
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| Source note | uspto-grants-2015_07 |
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