HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → HCID 86636109, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(Methylsulfonyl)phenol | HCID 123350 | — |
| Reactant | 4-chloro-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine | HCID 57964994 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86636109 | HCID 86636109 | 75.2% |
Reaction Conditions
| Temperature | 180 °C |
|---|
Reaction Steps
A mixture of 4-methanesulfonyl-phenol (available from Acros Organics, Geel, Belgium; 24 mg, 0.14 mmol), 4-chloro-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (Intermediate 22; 40 mg, 0.11 mmol) and potassium carbonate (19 mg, 0.14 mmol) in anhydrous DMF (2 mL) was heated in a Biotage Optimizer microwave at 180° C. for 10 min. The mixture was cooled and filtered through Celite, concentrated and held under vacuum. The residue was purified by flash column chromatography eluting with 0-3% methanol/dichloromethane to give 4-(4-methanesulfonyl-phenoxy-1-[1-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine (40 mg, 72%). Mass spectrum (ES) MH+=483.5.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08188098B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-5624edace2e645259b758657428709fe |
| Source note | uspto-grants-2012_05 |