20427-22-9

Usage

InChI:InChI=1/C6H6N4/c1-10-4-9-5-2-7-3-8-6(5)10/h2-4H,1H3

Upstream product

• 7013-21-0 2-Chloro-9-methyladenine 
• 120-73-0 purine 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 75-59-2 tetramethyl ammoniumhydroxide 
• 553-90-2 Dimethyl oxalate 
• 3013-82-9 6-N,N-dimethyl-9-methyladenine 
• 2009-52-1 N₆,N₉-dimethyladenine 
• 700-00-5 3-methyladenine 
• 64-18-6 formic acid 
• 13784-17-3 5-amino-4-methylaminopyrimidine 
• 186581-53-3 diazomethane 
• 84602-76-6 5-formamido-4-(methylamino)pyrimidine 

Downstream Products

• 13784-17-3 5-amino-4-methylaminopyrimidine 
• 874662-74-5 trans-[(amine)2(platinum(II))(μ-9-methylpurine-N7)Cl] perchlorate 
• 84602-76-6 5-formamido-4-(methylamino)pyrimidine 
• 33833-45-3 9-methyl-8-phenyl-9H-purine 

Relevant academic research and scientific papers

Alkylation with Oxalic Esters. Scope and Mechanism.

Alkyl oxalates are well suited for use as standard synthetic reagents in N-, O-, or S-alkylations and often display an interesting regioselectivity.The mechanism seems to be a direct alkylation of the substrate anion.

DEAMINATION, INVOLVING RING OPENING, IN REACTIONS OF 1-AMINOPURINIUM MESITYLENESULFONATES WITH METHANOLIC AMMONIA

On reaction of 1-aminopurinium mesitylenesulfonates with methanolic ammonia N-deamination occurs.For 1-amino-, 1-amino-8-(methylthio)-, 1-amino-8-phenyl-, 1-amino-2-methyl-, 1-amino-6-methyl- and 1-amino-8-phenyl-9-methylpurinium mesitylenesulfonate this reaction proceeds for at least 75percent via ring opening as shown by the isolation of 1-15N-labelled purines when 15N-labelled methanolic ammonia was used. 1-Amino-9-methylpurinium mesitylenesulfonate gave N-deamination without ring opening.The reaction of 1-amino-6-(methylthio)purinium mesitylenesulfonate with methanolic ammonia involves, besides deamination, partial substitution of the methylthio group; no ring opening is involved.However, ring opening followed by substitution occurs in the reaction of 1-amino-2-(methylthio)purinium mesitylenesulfonate; the reaction proceeds via an adduct at position 2.

A NEW SIMPLE PROCEDURE FOR ALKYLATION OF NITROGEN HETEROCYCLES USING DIALKYL OXALATES AND ALKOXIDES.

A variety of nitrogen heterocycles are N-alkylated in high yields with dialkyl oxalates and potassium alkoxides in refluxing dimethylformamide.

Studies of the Tautomerism of Purine and the Protonation of Purine and Its 7- and 9-Methyl Derivatives by Nitrogen-15 Nuclear Magnetic Resonance Spectroscopy

The nitrogen-15 NMR shifts of purine and its 7- and 9-methyl derivatives were measured at the natural-abundance level as a function of pH.The results made it possible for both the sites and magnitudes of protonation of purine and its derivatives to be determined.A semiquantitative determination was made of the position of the N7H-N9H tautomeric equilibria of purine in both water and dimethyl sulfoxide.

Methylathion of Heterocyclic Compounds Containing NH, SH and/or OH Groups by Means of N,N-Dimethylformamide Dimethyl Acetal

Methylations of heterocyclic systems, such as benzimidazole, naphthimidazole, imidazopyridine, purine, pyridine, pyrimidine, pyridazine and s-triazolopyridazine, which bore SH, NH and/or OH groups, were carried out with dimethylformamide dimethyl acetal to give the corresponding S-, N- and/or O-methyl derivatives in high yields.Selective methylation of some compounds containing both SH and NH groups took place to give first the S-methyl and subsequently the S,N-dimethyl derivatives.No side reactions, such as C-methylation, were observed.