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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1175520Generated: October 31, 2026

Hydrochloric Acid → HCID 59558816, compound

https://huagongshe.com/reaction/1175520

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantCesium carbonateHCID 10796—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
ReactantHCID 67051295HCID 67051295—
Reactant4-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidineHCID 86619877—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 59558816HCID 59558816—

Reaction Steps

A mixture of 3-hydroxy-3-methylazetidine-1-sulfonamide (0.25 g) (prepared according to patent WO 2004/011443), tris(dibenzylideneacetone)-dipalladium (0) (13 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (10 mg), cesium carbonate (0.68 g) was treated with a solution of 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine (the product of example 35 step i) (0.4 g) in dioxane (10 ml) and the whole then heated at reflux for 30 min. H2O (10 ml) was added followed by 1N hydrochloric acid solution (5 ml) and the resulting mixture extracted with EtOAc. The combined organic extracts were washed with saturated aqueous sodium chloride, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography on silica gel using EtOAc/DCM (1:4) as eluent to give the subtitle compound as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07838675B2
Source datasetuspto-grants-2010_11
ORD IDord-795100831b84432cb5ecd3ea39ef4efd
Source noteuspto-grants-2010_11