Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloroform | HCID 6212 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethynyl-3,5-dimethoxybenzene | HCID 4661321 | — |
| Reactant | HCID 178508725 | HCID 178508725 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178489940 | HCID 178489940 | 20.4% |
Reaction Steps
PdCl2(dppf)CH2Cl2 (163 mg) was added to a mixture of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (520 mg) synthesized by the method disclosed in WO 2007/126841, 1-ethynyl-3,5-dimethoxybenzene (504 mg), copper (I) iodide (57.3 mg), and triethylamine (0.56 ml) in DMF (10 ml). After nitrogen purging, the resulting mixture was stirred at 90° C. for 6 hours. Chloroform and water were added to the reaction mixture to separate the organic layer. After being washed with a saturated sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by basic silica gel column chromatography (developing solvent: chloroform/methanol) to obtain the title compound as a dark-brown solid (120 mg). Physical properties: m/z [M+H]+ 296.0
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09108973B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-8ead94e28d294fa0a4274beef02de758 |
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| Source note | uspto-grants-2015_08 |
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