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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1476631Generated: October 26, 2026

Cesium carbonate → HCID 67258156, compound

https://huagongshe.com/reaction/1476631

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant3,4-Difluorobenzeneboronic acidHCID 2734337—
ReactantTert-butyl 4-{6-bromo-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylateHCID 67258967—
CatalystDichlorobis(tricyclohexylphosphine)pallium (II)HCID 11050900—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 67258156HCID 67258156—

Reaction Steps

Tert-butyl 4-{6-bromo-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate (540 mg, compound B99), (3,4-difluorophenyl)boronic acid (158 mg), dichlorobis(tricyclohexylphosphine)palladium (37 mg) and aqueous cesium carbonate solution (489 mg, 2.0 M) in DME (10 ml) are reacted according to the procedure described in example B55 to afford the title compound after purification by flash column chromatography [silica gel, elution gradient: cyclohexane/EtOAc, 70/30 to 50/50 to 30/70 (v/v)] as a solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09018175B2
Source datasetuspto-grants-2015_04
ORD IDord-7943e00a905d42678a9b0d94645438ca
Source noteuspto-grants-2015_04