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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 717276Generated: October 31, 2026

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

https://huagongshe.com/reaction/717276

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 numberUS09193709B2
Source datasetuspto-grants-2015_11
ORD IDord-7c3ffc08744041e2872105829b6910fa
Source noteuspto-grants-2015_11