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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 535389Generated: October 30, 2026

Sodium Carbonate → 4-Chloro-6-(2-phenylethynyl)-5-pyrimidin-5-ylpyridin-2-amine

https://huagongshe.com/reaction/535389

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant(Pyrimidin-5-yl)boronic acidHCID 2795193—
Reactant5-Bromo-4-chloro-6-(2-phenylethynyl)pyridin-2-amineHCID 86694373—
CatalystHCID 178418397HCID 178418397—
SolventAcetonitrileHCID 6342—
Product4-Chloro-6-(2-phenylethynyl)-5-pyrimidin-5-ylpyridin-2-amineHCID 86694374—

Reaction Conditions

Temperature120 °C

Reaction Steps

A mixture of 5-bromo-4-chloro-6-(2-phenylethynyl)pyridin-2-amine C3a (1.0 g, 3.25 mmol), pyrimidin-5-ylboronic acid (604 mg, 4.88 mmol), Tetrakis(triphenylphosphine)palladium(0) (375 mg, 0.33 mmol), sodium carbonate (aqueous solution, 2 mol/l, 4.88 ml, 9.75 mmol) and ACN (15 ml) is stirred in a sealed tube at 120° C. until C3a is almost completely consumed. The mixture is then concentrated in vacuo and the product purified by NP chromatography. Yield: 420 mg (42%). HPLC-MS: M+H=307.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08859541B2
Source datasetuspto-grants-2014_10
ORD IDord-6877890640b84f28be9139d24c2da033
Source noteuspto-grants-2014_10