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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1405840Generated: October 25, 2026

Sodium Carbonate Decahydrate → 3-(4-(Cyclohexyloxy)phenyl)-5-methylpyrazin-2-amine

https://huagongshe.com/reaction/1405840

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium Carbonate DecahydrateHCID 151402—
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 6674841399.5%

Reaction Conditions

Temperature80 °C

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (0.922 g) was added to a suspension of 3-bromo-5-methylpyrazin-2-amine (5 g), 4-(cyclohexyloxy)phenylboronic acid (7.61 g) and sodium carbonate decahydrate (15.2 g) in DME (200 mL) and water (40 mL) and the mixture was stirred at 80° C. under nitrogen overnight. The insoluble material was removed by filtration (eluted with EtOAc), and silica-gel was added and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (7.5 g) as a pale orange solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08916551B2
Source datasetuspto-grants-2014_12
ORD IDord-0838caa213c649138b84d30e38253b0f
Source noteuspto-grants-2014_12