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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1405758Generated: October 25, 2026

Ethyl Acetate → 3-[6-(Cyclohexyloxy)pyridin-3-yl]-5-methylpyrazin-2-amine

https://huagongshe.com/reaction/1405758

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium CarbonateHCID 10340—
Reactant3-Chloro-5-methylpyrazin-2-amineHCID 15149676—
ReactantB-[6-(cyclohexyloxy)-3-pyridinyl]Boronic acidHCID 66747855—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
Product3-[6-(Cyclohexyloxy)pyridin-3-yl]-5-methylpyrazin-2-amineHCID 6674875585.6%

Reaction Conditions

Temperature90 °C

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (48.3 mg) was added to a suspension of 3-chloro-5-methylpyrazin-2-amine (200 mg), 6-(cyclohexyloxy)pyridin-3-ylboronic acid (339 mg) and sodium carbonate (295 mg) in DME (5 mL) and water (1 mL) and the mixture was stirred at 90° C. under nitrogen for 3 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) to give the title compound (339 mg) as light brown gum.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08916551B2
Source datasetuspto-grants-2014_12
ORD IDord-df7606dbbcf04b578d035e3365f28150
Source noteuspto-grants-2014_12