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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1622781Generated: November 1, 2026

Ethyl Acetate → 3-(4-(Cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine

https://huagongshe.com/reaction/1622781

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium CarbonateHCID 10340—
Reactant2-Amino-3-bromo-5-methylpyrazineHCID 9899043—
Reactant4-Cyclohexyloxy-benzeneboronic acidHCID 22289818—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
Product3-(4-(Cyclohexyloxy)phenyl)-5-methylpyrazin-2-amineHCID 6674841352.2%

Reaction Conditions

Temperature100 °C

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (55.3 mg) was added to a suspension of 3-bromo-5-methylpyrazin-2-amine (300 mg), 4-(cyclohexyloxy)phenylboronic acid (456 mg) and sodium carbonate (338 mg) in DME (15 mL) and water (3 mL) and the mixture was stirred at 100° C. under nitrogen for 2 hr. Water and EtOAc were added and the organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) and washed with hexane/IPE to give the title compound (236 mg) as a white powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08778934B2
Source datasetuspto-grants-2014_07
ORD IDord-d1d26cd03e2145979aca1b8a7310456f
Source noteuspto-grants-2014_07