1127-75-9

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 116, p. 9331, 1994 DOI: 10.1021/ja00099a061

InChI:InChI=1/C7H8N4S/c1-11-4-10-5-6(11)8-3-9-7(5)12-2/h3-4H,1-2H3

Upstream product

• 2346-74-9 6-chloro-9-methyl-9H-purine 
• 74-93-1 methylthiol 
• 1006-20-8 9-methyl-1,9-dihydro-6H-purine-6-thione 
• 74-88-4 methyl iodide 
• 99669-50-8 N-(4-methylamino-6-methylsulfanyl-pyrimidin-5-yl)-formamide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 157930-09-1 6-Mercaptopurine 
• 50-66-8 6-methylthiopurine 
• 158782-61-7 9-methyl-6-(1,2,4-triazol-4-yl)purine 
• 5188-07-8 sodium thiomethoxide 
• 74-87-3 methylene chloride 
• 74-83-9 methyl bromide 
• 52602-71-8 N⁴-methyl-6-methylsulfanyl-pyrimidine-4,5-diamine 
• 52602-68-3 6-chloro-N⁴-methylpyrimidine-4,5-diamine 

Downstream Products

• 2009-52-1 N₆,N₉-dimethyladenine 

Relevant academic research and scientific papers

Regioselective alkylation reaction of purines under microwave irradiation

The alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylati

Nucleic acid related compounds. 86. Nucleophilic functionalization of adenine, adenosine, tubercidin, and formycin derivatives via elaboration of the heterocyclic amino group into a readily displaced 1,2,4-triazol-4-yl substituent

Treatment of 9-methyladenine and hydroxyl-protected derivatives of adenosine and 2′-deoxyadenosine with 1,2-bis[(dimethylamino)methylene]hydrazine and/or its dihydrochloride at elevated temperatures in appropriate solvents resulted in elaboration of the 6-amino group into a 6-(1,2,4-triazol-4-yl) substituent in excellent yields. Analogous functionalization of the amino groups of tubercidin {4-amino-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]-pyrimidine} and formycin {7-amino-3-(β-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidine} gave the respective 4- and 7-(1,2,4-triazol-4-yl) derivatives. Nucleophilic replacement of the triazole moiety gave the respective 6-, 4-, and 7-substituted purine, pyrrolo[2,3-d]pyrimidine, and pyrazolo[4,3-d]pyrimidine products. This first general method for "direct" nucleophilic replacement of an amino group on these nitrogen heterocycles also provides a new class of compounds for potential postsynthetic modifications after incorporation into oligonucleotides.

Synthesis and Properties of Purinophanes: Relationship between the Magnitude of Hypochromism and Stacking Geometry of Purine Rings

Twelve purinophanes 1-12, in which two purine rings are fixed with different modes of stacking by two or three polymethylene chains, have been prepared by either stepwise introduction of the linking chains or quasi-dimerization of disubstituted purine der

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.