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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2267357Generated: October 25, 2026

Sodium Carbonate → 5-(2-Chloropyrimidin-4-yl)thiophene-2-carbonitrile

https://huagongshe.com/reaction/2267357

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1,4-DioxaneHCID 31275—
Reactant2,4-DichloropyrimidineHCID 77531—
Reactant5-Cyanothiophene-2-boronic acidHCID 4198743—
CatalystHCID 178418476HCID 178418476—
SolventMethanolHCID 887—
SolventDichloromethaneHCID 6344—
Product5-(2-Chloropyrimidin-4-yl)thiophene-2-carbonitrileHCID 57428836—

Reaction Conditions

Temperature140 °C

Reaction Steps

A solution of 0.22 g (1.4 mmol) of 5-cyanothiophen-2-ylboronic acid, 0.21 g (1.4 mmol) of 2,4-dichloropyrimidine and 49 mg (0.070 mmol) of bis(triphenylphosphine)palladium(II) chloride in 2 mL of a 2 M Na2CO3 aqueous solution and 5 mL of 1,4-dioxane was as heated in a microwave for 30 min at 140° C., then cooled to rt, diluted with CH2Cl2 and MeOH, and dried over MgSO4. The organic solvent was removed in vacuo, and the resulting solid was purified by flash chromatography eluting with a linear gradient of 50% EtOAc in hexane to neat EtOAc to deliver the title compound. MS (M+H)+ 222.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07858785B2
Source datasetuspto-grants-2010_12
ORD IDord-8936163b2f184a618c1cf9619478f6ac
Source noteuspto-grants-2010_12