1127-75-9Relevant articles and documents
Efficient conversion of 6-aminopurines and nucleosides into 6-substituted analogues via novel 6-(1,2,4-triazol-4-yl)purine derivatives
Samano, Vicente,Miles, Robert W.,Robins, Morris J.
, p. 9331 - 9332 (1994)
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Holy
, p. 585 (1972)
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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
Miles, Robert W.,Samano, Vicente,Robins, Morris J.
, p. 5951 - 5957 (2007/10/02)
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.
Methylathion of Heterocyclic Compounds Containing NH, SH and/or OH Groups by Means of N,N-Dimethylformamide Dimethyl Acetal
Stanovnik, Branko,Tisler, Miha,Hribar, Alenka,Barlin, Gordon B.,Brown, Desmond J.
, p. 1729 - 1738 (2007/10/02)
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.
