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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1527640Generated: November 3, 2026

1,2-Dimethoxyethane → 4-Chloro-5-ethyl-6-(furan-2-yl)-pyrimidine

https://huagongshe.com/reaction/1527640

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DimethoxyethaneHCID 8071—
ReactantSodium CarbonateHCID 10340—
ReactantFuran-2-boronic acidHCID 2734357—
Reactant4,6-Dichloro-5-ethylpyrimidineHCID 21828432—
SolventWaterHCID 962—
Product4-Chloro-5-ethyl-6-(furan-2-yl)-pyrimidineHCID 6564541651.4%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 4,6-dichloro-5-ethylpyrimidine (10 g), 2-furylboronic acid (6.33 g) tetrakis(triphenylphosphine)palladium (1.94 g), dimethoxyethane (100 ml), and sodium carbonate solution (2 mol/l) (60 ml) was stirred at 70° C. for 2 hours and at 80° C. for 2 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 6.06 g of 4-chloro-5-ethyl-6-(furan-2-yl)-pyrimidine.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09089136B2
Source datasetuspto-grants-2015_07
ORD IDord-96d52de5ab5e426297f083d43a7a73b9
Source noteuspto-grants-2015_07