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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1945672Generated: October 25, 2026

Cesium carbonate → HCID 59606001, compound

https://huagongshe.com/reaction/1945672

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant2-EthylbenzimidazoleHCID 15807—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
Reactant4-{1-[2-Chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purin-8-ylmethyl]azetidin-3-yl}piperazin-2-oneHCID 59606010—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 59606001HCID 5960600139.1%

Reaction Conditions

Temperature115 °C

Reaction Steps

A mixture of 4-{1-[2-chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purin-8-ylmethyl]azetidin-3-yl}piperazin-2-one (990 mg, 2.00 mmol), 2-ethylbenzimidazole (322 mg, 2.20 mmol), tris(dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol), XPhos (95 mg, 0.20 mmol) and Cs2CO3 (980 mg, 3.01 mmol) in dioxane (30 mL) was purged with argon then heated at 115° C. for 6 h then stirred at r.t. for 16 h. The reaction mixture was filtered through Celite®, washing with dioxane, and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound (470 mg, 39%). LCMS (method A): RT 2.01 and 1.92 min [M+H]+ 601.6

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08394796B2
Source datasetuspto-grants-2013_03
ORD IDord-8c9138a90fd34f468cded2cd828c0ad8
Source noteuspto-grants-2013_03