25911-65-3

Usage

Uses

3-Aminopyrazine-2-carbonitrile is a useful synthesis reagent.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 26, p. 817, 1989 DOI: 10.1002/jhet.5570260357

InChI:InChI=1/C5H4N4/c6-3-4-5(7)9-2-1-8-4/h1-2H,(H2,7,9)

Upstream product

• 32587-10-3 3-aminopyrazine-2-carboxamide 
• 14036-06-7 diethoxymethyl acetate 
• 76952-35-7 2-aminopyrazine-3-carboxamide oxime 
• 35336-09-5 dimethylaminoacrolein diethylacetal 
• 20893-01-0 ({[(4-methylphenyl)sulfonyl]oxy}imino)malononitrile 
• 77119-92-7 2-((Z)-2-Dimethylamino-vinylimino)-malononitrile 
• 76952-40-4 4-aminopteridine 3-oxide 
• 83410-14-4 2-amino-3-(1',2',4'-oxadiazolyl-3')pyrazine 
• 86805-19-8 4-(N,N-dimethylaminomethyleneamino)pteridine 3-oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 6863-77-0 3-aminopyrazine 1-oxide 
• 143-33-9 sodium cyanide 
• 34859-38-6 2-Cyano-3-<(dimethylaminomethylene)amino>pyrazine 
• 67-56-1 methanol 

Downstream Products

• 71898-69-6 2-acetylaminopyrazine-3-carboxamide 
• 85123-93-9 2-benzoylamino-3-cyanopyrazine 
• 147425-71-6 2-acetyl-6-amino-5-cyanopyrazine 
• 81411-78-1 3-cyano-2(1H)-pyrazinone 
• 76952-35-7 2-aminopyrazine-3-carboxamide oxime 
• 160892-17-1 2-amino-3-<3-(2-fluorophenyl)-1H-<1,2,4>triazol-5-yl>pyrazine 
• 114953-93-4 2-amino-3-(3-phenyl-1H-<1,2,4>triazol-5-yl)pyrazine 
• 133915-22-7 4-amino-2-(benzyloxymethyl)pteridine 
• 133915-37-4 4-amino-2-[(4-methylphenoxy)methyl]pteridine 
• 133915-36-3 4-amino-2-[(4-methoxyphenoxy)methyl]pteridine 
• 133915-33-0 4-amino-2-[(3,4-dichlorophenoxy)methyl]pteridine 
• 1127-93-1 2,4-diaminopteridin 
• 32587-10-3 3-aminopyrazine-2-carboxamide 
• 700-47-0 pteridin-4-one 

Relevant academic research and scientific papers

Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas as potent inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2)

Novel 1-(2-aminopyrazin-3-yl)methyl-2-thioureas are described as inhibitors of mitogen-activated protein kinase-activated protein kinase 2 (MK-2). These compounds demonstrate potent in vitro activity against the enzyme with IC50 values as low as 15 nM, and suppress expression of TNFα in THP-1 cells and in vivo in an acute inflammation model in mice. The synthesis, structure-activity relationship (SAR), and biological evaluation of these compounds are discussed.

Kinase inhibitors and methods of use thereof

Compositions and methods and are provided for treating disorders associated with compromised vasculostasis. Invention methods and compositions are useful for treating a variety of disorders including for example, stroke, myocardial infarction, cancer, isc

Syntheses of 1-allyl-6-(arylamino)methyl-7-methyl-3-phenylpteridine-2,4-dione, a methanopterin analogue

The nucleophilic substitution of 2,3-dicyanopyrazine (1) with allylamine is useful for the construction of pteridine ring. A methanopterin analogue, 1-allyl-6-(mesitylamino)methyl-7-methy-3-phenylpteridine (12), was synthesised by this method from 2,3-dic

Studies on Pyrazines. 24. A Simple and Versatile Synthetic Method for 3-Alkoxy- and 3-Aminopyrazinecarbonitriles

New and concise synthetic methods of 3-alkoxy- and 3-aminopyrazinecarbonitriles by nucleophilic displacement of 3-phenylsulfonylpyrazinecarbonitriles are reported.

Studies on Pyrazines. Part 22. Lewis Acid-Mediated Cyanation of Pyrazine N-Oxides with Trimethylsilyl Cyanide: New Route to 2-Substituted 3-Cyanopyrazines

Reaction of 3-substituted pyrazine 1-oxides with trimethylsilyl cyanide in the presence of triethylamine in acetonitrile gave the corresponding cyanopyrazines, yields of which depended remarkably on the substituent.Electron-donating groups enhanced the cyanation with high regioselectivity to 2-substituted 3-cyanopyrazines, while a chloro substituent suppressed the conversion.Addition of zinc halide to the reaction mixture, in most cases, increased the reactivity and improved the regioselectivity.On the other hand, the N-oxides carrying an electron-withdrawing methoxycarbonyl or N-butylcarbamoyl group underwent the cyanation, without need for the Lewis acid, to provide a mixture of nearly equal amounts of 2-substituted 3- and 5-cyanopyrazines.The latter compound was exclusively obtained when 3-methoxycarbonyl- or 3-cyanopyrazine 1-oxide was treated with diethoxyphosphoryl cyanide.

Studies on Pyrazines. 18 . A New and Convenient Synthesis of 2-Amino-3-cyanopyrazine

The titled compound, 2-amino-3-cyanopyrazine (1), was prepared by reaction of 3-aminopyrazine 1-oxide (7) with trimethylsilyl cyanide.Furthermore, conditions of individual steps in synthetic route to 7 starting from 2-pyrazinecarboxamide were optimized.

RING TRANSFORMATIONS OF SOME 4-AMINOPTERIDINE 3-OXIDES AND DERIVATIVES

Syntheses of 4-aminopteridine 3-oxides are described.The pyrimidine part undergoes transformations with various reagents to give 4-hydroxyaminopteridines, substituted pyrazines, or substituted 1,2,4-oxadiazolylpyrazines. s-Triazolo(1,5-a)pyrazines can be prepared from 1,2,4-oxadiazolylpyrazines.The ring opening of the pyrimidine part of pteridines proceeds either py a C2-N3 or N3-C4 bond cleavage.

Syntheses and Transformations of Some 1,2,4-Oxadiazolylpyrazines

Cyanopyrazines with an ortho-amino, oxo and other groups are transformed into the corresponding amidoximes.From these the corresponding 1,2,4-oxadiazolyl derivatives can be prepared and interconversions to the corresponding pteridine 3-oxides are described.

SOME NEW SYNTHETIC APPROACHES FOR THE PREPARATION OF PTERIDINE-3-OXIDES AND PTERIDINES

Starting from 2-amino-3-cyanopyrazine some new syntheses of 4-substituted pteridines and pteridine-3-oxides have been devised.

NOUVELLE VOIE D'ACCES AU DIETHYLACETAL DE L'AMINO-2 CYANO-3 FORMYL-5 PYRAZINE

An unequivocal two step synthesis of 2-amino-3-cyano-5-formylpyrazine diethylacetal, starting from dimethylaminoacrolein and O-tosylisonitrosomalononitrile, is described.This pyrazine is a key intermediate for the preparation of folic acid and various analogues.