Back
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

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantBinap, (A+-)-HCID 634876—
Reactant2,3-Dimethyl-6-amino-2H-indazole hydrochlorideHCID 46864001—
ReactantTert-butyl 9((2-chloro-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylateHCID 118390073—
Catalystpalladium(II) acetateHCID 167845—
Solvent1,4-DioxaneHCID 31275—
Producttert-butyl 9-((2-((2,3-dimethyl-2H-indazol-6-yl)amino)-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecane-3-carboxylateHCID 11839017866.7%

Reaction Conditions

Temperature150 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09399637B2
Source datasetuspto-grants-2016_07
ORD IDord-55fd4c9b2b0f4954b1eaf4908d6c6dad
Source noteuspto-grants-2016_07