HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 3-((4-Amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-4-phenyl-1H-isochromen-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Fluoro-5-hydroxybenzeneboronic acid | HCID 44717308 | — |
| Reactant | 3-((4-Amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-4-phenyl-1H-isochromen-1-one | HCID 118131046 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-((4-Amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-4-phenyl-1H-isochromen-1-one | HCID 118131396 | 12.4% |
Reaction Steps
3-((4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-4-phenyl-1H-isochromen-1-one (intermediate D1, 50 mg, 0.101 mmol), 3-fluoro-5-hydroxyphenylboronic acid (32 mg, 0.201 mmol), Cs2CO3 (69 mg, 0.202 mmol), Pd(PPh3)4 (9.3 mg, 8.0 umol), were reacted in DMF (0.5 mL) at 110° C. under mw irradiation. The resulting crude was straightforward purified via reverse phase chromatography using a Biotage C18 30 g SNAP with a gradient of water and acetonitrile to give the title compound (6 mg, 12%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321776B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-122be676c26448168f1356c55c199605 |
| Source note | uspto-grants-2016_04 |