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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 335179Generated: October 30, 2026

Phenol → 5-Bromo-3-phenoxypyrazin-2-amine

https://huagongshe.com/reaction/335179

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhenolHCID 996—
ReactantEthyl AcetateHCID 8857—
ReactantSodium hydrideHCID 24758—
Reactant2-Amino-3,5-dibromopyrazineHCID 620004—
SolventTetrahydrofuranHCID 8028—
Product5-Bromo-3-phenoxypyrazin-2-amineHCID 1795602164.6%

Reaction Steps

Added sodium hydride (0.348 g, 8.70 mmol) to a solution of phenol (0.819 g, 8.70 mmol) in THF (50 mL) at 0° C. and stirred 30 minutes. Added 3,5-dibromopyrazin-2-amine (2.00 g, 7.91 mmol) in THF (10 mL). Removed the ice bath and refluxed overnight. Partitioned between ethyl acetate and water, washed with brine, dried, and concentrated. Purified by MPLC (Biotage) eluting with 5:1 hexane:ethyl acetate to afford the title compound (1.36 g, 64.6% yield) as a light yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08883828B2
Source datasetuspto-grants-2014_11
ORD IDord-3e574ba7a29c4ba497c42a3d72ab1c9b
Source noteuspto-grants-2014_11