HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1056649Generated: November 1, 2026
Cesium carbonate → tert-butyl 9-((2-((2,3-dimethyl-2H-indazol-6-yl)amino)-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate
https://huagongshe.com/reaction/1056649
Participants
| Role | Name | HCID | Charge |
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| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 2,3-Dimethyl-6-amino-2H-indazole hydrochloride | HCID 46864001 | — |
| Reactant | Tert-butyl 9((2-chloro-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate | HCID 118390073 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | tert-butyl 9-((2-((2,3-dimethyl-2H-indazol-6-yl)amino)-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate | HCID 118390178 | 66.7% |
Reaction Steps
A mixture of tert-butyl 9-((2-chloro-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylate (1.2 g, 3.0 mmol), 2,3-dimethylindazol-6-amine hydrochloride (896.5 mg, 4.536 mmol), diacetoxypalladium (132.4 mg, 0.5898 mmol), BINAP (370.3 mg, 0.5947 mmol) and dicesium carbonate (2.98 g, 9.15 mmol) was dissolved in anhydrous dioxane (10 mL). The reaction mixture was stirred under microwave irradiation at 150° C. for 2 h and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1) to give the title compound as a yellow solid (1.04 g, 66%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09399637B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-55fd4c9b2b0f4954b1eaf4908d6c6dad |
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| Source note | uspto-grants-2016_07 |
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