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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1674395Generated: October 25, 2026

4-Isopropoxybenzeneboronic acid → 4'-{[4-ethyl-5-(4-isopropoxyphenyl)-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrile

https://huagongshe.com/reaction/1674395

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Isopropoxybenzeneboronic acidHCID 3698726—
Reactant4'-[(5-bromo-4-ethyl-6-oxo-2-propylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrileHCID 57460066—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
SolventEthyl AcetateHCID 8857—
SolventCesium carbonateHCID 10796—
Solvent1,4-DioxaneHCID 31275—
Product4'-{[4-ethyl-5-(4-isopropoxyphenyl)-6-oxo-2-propylpyrimidin-1(6H)-yl]methyl}biphenyl-2-carbonitrileHCID 5746041989%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of (4-isopropoxyphenyl)boronic acid (0.31 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (0.05 g) and 4′-[(5-bromo-4-ethyl-6-oxo-2-propylpyrimidin-1(6H)-yl)methyl]biphenyl-2-carbonitrile (0.5 g) in 1,4-dioxane (10 mL) and 2 M cesium carbonate (2 mL) was stirred overnight at 100° C. under an argon atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.50 g, 89%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07998968B2
Source datasetuspto-grants-2011_08
ORD IDord-1de89e87ff42483aae61f0822fc1877c
Source noteuspto-grants-2011_08