Purine, 6-methylamino

Purine, 9-methyl-6-methylamino-synthesis, 5, 570 Purine, 3-methyl-6-methylthio-irradiation, 5, 543 synthesis, 5, 535, 595... 

Chemical Name 3,7-Dihydro-8-[(2-hydroxyethyl)methylamino]-1,3,7-trimethyl-l H-purine-2,6-dione... 

H-Purin und 6-Amino-purin (unter Ammoniak-Abspaltung) liefern in waBrigen Puf-ferlosungen an Quecksilber l,2,3,6-Tetrahydro-9H-purin, das zu 5-Amino-4-(hydroxy-methylamino-methyl)-imidazol hydrolysiert werden kann2. 

A one-pot procedure for the transformation of 6-thiopurine nucleosides to 6-aminopurines was developed using DMDO as the oxidant in the presence of a stoichiometric amount of various amines <1996T6759>. For example, 6-thio-9-(2, 3, 5 -tri-0-acetyl-/3-D-ribosyl)purine was readily converted to the 6-alkylamino derivatives (6-amino, 75% yield 6-methylamino, 55% yield). Similarly, A -6-acetyl-8-thio-9-(2, 3, 5 -tri-0-acetyl-/3-D-ribosyl)adenosine was converted to A -6-acetyl-8-methylamino-9-(2, 3, 5 -tri-0-acetyl-/3-D-ribosyl)adenosine (DMDO, methylamine, CH2CI2, 25 °C, 83% yield). Less nucleophilic 2-mercaptopurine derivatives did not undergo the displacement reaction, however, and only the products of dithiane formation and desulfurization were isolated. 

Pyrimidin-5-amine, 4-methylamino-synthesis, 3, 121 Pyrimidin-5-amine, 4-oxo-purine synthesis from, S, 582 Pyrimidinamines acylation, 3, 85 alkylation, 3, 86 basic pKa, 3, 60-61 diazotization, 3, 85 Dimroth rearrangement, 3, 86 electrophilic reactions, 3, 68 Frankland-Kolbe synthesis, 3, 116 hydrolysis, 3, 84 IR spectra, 3, 64 15N NMR, 3, 64 nitration, 3, 69 Principal Synthesis, 3, 129 reactivity, 3, 84-88 structure, 3, 67 synthesis, 3, 129 Pyrimidin-2-amines alkylation, 3, 61, 86 basic pKa, 3, 60 diazotization, 3, 85 hydrogenation, 3, 75 hydrolysis, 3, 84 mass spectra, 3, 66 Pyrimidin-4-amines acidity, S, 310 alkylation, 3, 61, 86 basic pKa, 3, 61 Schiff base, 3, 85 synthesis, 3, 110, 114 1,3,5-triazines from, 3, 518 Pyrimidin-5-amines basic pKa, 3, 61 hydrogenation, 3, 75 reactions... 

Chemical Name 3-Pyridine carboxylic acid compounded with 3,7-dihydro-7-[2-hydroxy-3-[(2-hydroxymethyl)methylamino]propyl]-l,3-dimethyl-lH-purine-2,6-dione (1 1)... 

Escherichia coli B was incubated with 2,6-diaminopurine (XXIV), and 6-amino-2-(methylamino)-9-(5-0-phospho-D-ribosyl)purine (XXV) was isolated from the acid-soluble extract of the cells. 5-Nucleotidase liberated a nucleoside containing D-ribose. Hydrolysis of the nucleoside (or nucleotide) with N hydrochloric acid liberated 6-amino-2-(methylamino)purine, which was identified by paper chromatography and by its ultraviolet absorption spectrum. The chromatographic and ion-exchange behavior of the extract also suggested the presence of either a pyrophosphate or a triphosphate of the 6-amino-2-methylamino-(D-ribosyl)purine. In a similar manner, 2,6-diamino-9-(5-0-phospho-D-ribosyl)purine (XXVI) was isolated and identified, together with its possible pyrophosphate or triphosphate. 2,6-... 

A mutant of Escherichia coli B, resistant to 2,6-diaminopurine, was found to convert this base to 6-amino-2-methylamino-purine (XXVII) at a rate 60 to 90 % of that of normal cells. The methylated base was isolated from the culture medium, but the organism lacked the ability to incorporate 2,6-diaminopurine or its A-methyl derivative into the nucleotide fraction of the cell. This observation supports previous data which had indicated that resistance to this substance in Lactobacillus casei is due to the loss of an enzyme system responsible for the incorporation of the base into the nucleotide. ... 

Addition of adenine prevents the inhibiting effect of 2,6-diaminopurine, as well as blocking the formation of the nucleotides of 2,6-diaminopurine and 6-amino-2-methylamino-purine. 

The synthesis of 6-amino-2-methylamino-purine from 2,6-diamino-purine and the corresponding nucleotides was also demonstrated in crude extracts of Escherichia coli B. 

Aminopurines have usually been prepared from 8-chloropurines as in the amination of 8-chlorocaffeine to 8-aminocaffeine (1882LA(2 15)265), or alternatively from 8-methyl-thiopurine as in the synthesis of 8-amino-, 8-methylamino- or 8-dimethylamino-purine from 8-methylthiopurine with ammonia, methylamine or dimethylamine, respectively (54JCS2060). A good yield of 8-amino-6-oxo-l,6-dihydropurine was obtained in a Traube synthesis from 4,5-diamino-6-oxo-l,6-dihydropyrimidine and guanidine at 200 °C (58JA6671). 

Heating l,3-dimethyl-5-nitrosouracil-6-amine with tosyl chloride in dimethylformamide at 230 "C causes separation of 8-(methylamino)theophylline (4) as the major product. A reaction mechanism via the formation of purin-8-amine 7-oxide is proposed. 8-(Mcthylamino)-theophylline (4) can also be prepared by condensation of the ainiiionilrosouracil with tosyl chloride in methylformamide. ... 

Bis(hydroxymethyl)phosphonic acid esters that incorporated thymine were employed as a backbone to prepare short oligonucleotide chains. This chain was prepared by condensation of the bis(4,4 -dimethoxytrityl) protected phosphonic acid and iV or N -(2-hydroxyethyl)thymine in the presence of l-(2-mesitylenesul-fonyl)-3-nitro-l,2,4-triazole or by an Appel reaction with or N -(2-aminoethyl)thymine (89a-h). Selective removal of one DMT-group and phos-phitylation yielded the building blocks for solid supported synthesis of the short oligomers by the phosphoramidite approach. Holy has reported the synthesis of 8-amino and 8-substituted amino derivatives of acyclic purine nucleotide analogues. The 8-amino, 8-methylamino- and 8-dimethylamino-adenine and -guanine analogues of iV-(2-phosphonomethoxyethyl) and (S)-iV-(3-hydroxy-2-phosphono-methoxy-propyl) derivatives of purines (90a-i), were prepared by... 

Thymine (T) Cytosine (C) Adenine (A) Guanine 5-Hydroxymethyl-uracil (HMU) 6-Methylamino-purine (HMA)... 

The preparation of 9-niethyl and 9-butyl-2-hydroxy-8,9-dihydro-7H-purine-8-thione (XXVa Table 7) is somewhat unusual. Brown [45) has obtained these compounds from carbon disulfide and respectively f-methyl and 1 -butyl-5,6-diamino-1,2-dihydropyrimidin-2-one (XXIVa.). Evidently a shift of the alkyl group from the 3-N to the 9 N atom must occur during the ring closure. The structure of these two purines has been confirmed by their independent synthesis from 4-methylamino and 4-butylamino-5-amino-2-hydroxy pyrimidine. 

An analogous structure, l,4,4a,5,6,7-hexahydro-l,4,4a-trimethyl-9//-pyrrolo-[l,2-a]purin-9-one (5), can be prepared by cyclization of a caffeidine homologue, 1-methyl-4-methylamino-imidazole-5-[7V-(4-oxopentyl)carboxamide] (4) in ethanolic hydrogen chloride (Scheme 2). The vasodilatation activity of compound 5 was reported in (86CPB36). 

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