1-(2-Pyrimidinylamino)pyridinium Inner Salt

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(reagent for the formation of imidazo[1,2-α]pyrimidines1 and 2-aminopyrimidines2)

Alternate Name: pyridinium N-(2-pyrimidinyl) aminide.

Physical Data: mp 151–153 °C.3

Solubility: soluble in acetonitrile, ethanol, 1-4-dioxane, chloroform, and dichloromethane.

Form Supplied in: yellow solid.

Preparative Methods: the title reagent can be prepared from N-aminopyridinium iodide4 and 2-chloropyrimidine5 with potassium carbonate in acetonitrile,3 or in water under microwave irradiation.6 Alternatively, the title compound can be prepared by a multistep synthesis. Reaction of 2-hydrazinyl pyrimidine with 2,4-dinitrophenylpyridinium chloride affords a hydrazone that is then heated in acetic acid and the resulting salts are then deprotonated with potassium carbonate.7

Purification: recrystallization from EtOAc.3

Handling, Storage, and Precautions: bench-stable with no particular precautions identified.
Original languageEnglish
Title of host publicatione-EROS Encyclopedia of Reagents for Organic Synthesis
ISBN (Electronic)9780470842898
Publication statusPublished - 11 Apr 2017


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