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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 539669Generated: October 27, 2026

1,2-Dimethoxyethane → Methyl 2-(6-chloropyrimidin-4-yl)benzoate

https://huagongshe.com/reaction/539669

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DimethoxyethaneHCID 8071—
ReactantSodium CarbonateHCID 10340—
Reactant2,4-DichloropyrimidineHCID 77531—
ReactantMethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 2760076—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
ProductMethyl 2-(6-chloropyrimidin-4-yl)benzoateHCID 2490204931.6%

Reaction Conditions

Temperature150 °C

Reaction Steps

A mixture of methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (2.0 g), 2,6-dichloropyrimidine (1.4 g), sodium carbonate (2.4 g), tetrakis(triphenylphosphine)palladium(0) (0.44 g), water (2.0 mL) and DME (10 mL) was stirred at 150° C. for 1 hr under microwave irradiation. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.60 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08871766B2
Source datasetuspto-grants-2014_10
ORD IDord-4e6aca1aaa654062b709c32b27edd4bb
Source noteuspto-grants-2014_10