1-(2-Pyrimidinylamino)pyridinium Inner Salt

Paul Davies

doi:10.1002/047084289X.rn02042

1-(2-Pyrimidinylamino)pyridinium Inner Salt

Paul Davies

Chemistry

Research output: Chapter in Book/Report/Conference proceeding › Entry for encyclopedia/dictionary

Abstract

(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 language	English
Title of host publication	e-EROS Encyclopedia of Reagents for Organic Synthesis
Publisher	Wiley
ISBN (Electronic)	9780470842898
DOIs	https://doi.org/10.1002/047084289X.rn02042
Publication status	Published - 11 Apr 2017

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10.1002/047084289X.rn02042

1 Article
1 Review article

Nucleophilic nitrenoids through π-acid catalysis: providing a common basis for rapid access into diverse nitrogen heterocycles
Davies, P. & Garzon Sanz, M., Aug 2015, In: Asian Journal of Organic Chemistry. 4, 8, p. 694-708 15 p.
Research output: Contribution to journal › Review article › peer-review

Open Access
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76 Citations (Scopus)

241 Downloads (Pure)
A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition
Garzon, M. & Davies, P. W., 19 Sept 2014, In: Organic Letters. 16, 18, p. 4850-3 4 p.
Research output: Contribution to journal › Article › peer-review

Open Access
File
62 Citations (Scopus)

176 Downloads (Pure)

Cite this

@inbook{9bc6cfdce6ba49229ab55303bd1be8c2,

title = "1-(2-Pyrimidinylamino)pyridinium Inner Salt",

abstract = "(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.3Solubility: 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.7Purification: recrystallization from EtOAc.3Handling, Storage, and Precautions: bench-stable with no particular precautions identified.",

author = "Paul Davies",

year = "2017",

month = apr,

day = "11",

doi = "10.1002/047084289X.rn02042",

language = "English",

booktitle = "e-EROS Encyclopedia of Reagents for Organic Synthesis",

publisher = "Wiley",

}

TY - CHAP

T1 - 1-(2-Pyrimidinylamino)pyridinium Inner Salt

AU - Davies, Paul

PY - 2017/4/11

Y1 - 2017/4/11

N2 - (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.3Solubility: 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.7Purification: recrystallization from EtOAc.3Handling, Storage, and Precautions: bench-stable with no particular precautions identified.

AB - (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.3Solubility: 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.7Purification: recrystallization from EtOAc.3Handling, Storage, and Precautions: bench-stable with no particular precautions identified.

U2 - 10.1002/047084289X.rn02042

DO - 10.1002/047084289X.rn02042

M3 - Entry for encyclopedia/dictionary

BT - e-EROS Encyclopedia of Reagents for Organic Synthesis

PB - Wiley

ER -

1-(2-Pyrimidinylamino)pyridinium Inner Salt

Abstract

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Research output

Nucleophilic nitrenoids through π-acid catalysis: providing a common basis for rapid access into diverse nitrogen heterocycles

A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition

Cite this