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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 632619Generated: October 30, 2026

Dimethylformamide → HCID 86682473, compound

https://huagongshe.com/reaction/632619

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantSodium CarbonateHCID 10340—
Reactant5-Bromo-2-chloropyrimidineHCID 606665—
Reactant3-(Methoxycarbonyl)benzeneboronic acidHCID 2734714—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
ProductHCID 86682473HCID 8668247328.3%

Reaction Conditions

Temperature110 °C

Reaction Steps

To 2 ml of N,N-dimethylformamide deaerated with argon for 10 minutes, 213 mg (1.10 mmol) of 5-bromo-2-chloropyrimidine, 181 mg (1.05 mmol) of 3-(methoxycarbonyl)phenylboronic acid, 315 mg (2.97 mmol) of sodium carbonate and 22.4 mg (0.100 mmol) of palladium acetate were added, and the mixture was stirred at 110° C. for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with toluene three times. The obtained organic phases were combined, washed with saturated sodium chloride aqueous solution, dried with magnesium sulfate and then filtered, and the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=92/8-76/24 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 74 mg of the title compound as a white solid (yield: 28%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09321747B2
Source datasetuspto-grants-2016_04
ORD IDord-51b49a2cc5904681a7e0b127d9a4d18f
Source noteuspto-grants-2016_04