HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 118390048, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 5-Cyclopropyl-1H-pyrazol-3-amine--hydrogen chloride (1/1) | HCID 16495339 | — |
| Reactant | Tert-butyl 3-[(2,5-dichloropyrimidin-4-yl)amino]-9-azaspiro[5.5]undecane-9-carboxylate | HCID 118390013 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 118390048 | HCID 118390048 | 59.5% |
Reaction Steps
A solution of tert-butyl 9-((2,5-dichloropyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate (506 mg, 1.22 mmol), 5-cyclopropyl-1H-pyrazol-3-amine hydrochloride (272 mg, 1.70 mmol), cesium carbonate (1.176 g, 3.609 mmol), [1-(2-diphenylphosphanyl-1-naphthyl)-2-naphthyl]-diphenyl-phosphane (147.6 mg, 0.2370 mmol) and diacetoxypalladium (53.8 mg, 0.240 mmol) in anhydrous dioxane (10 mL) stirred in a sealed tube under the microwave radiation at 150° C. for 2 h. Then the reaction mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1) to give the title compound as a light yellow solid (364 mg, 59.5%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09403801B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-4f290108bc6044ea83366bb703a23428 |
| Source note | uspto-grants-2016_08 |