6-Dimethylamino-9- purine

Purine, 1,6-dihydro-8,9-dimethyl-6-thioxo-synthesis, 5, 583 Purine, 2,6-dimethoxy-synthesis, 5, 596 Purine, 2,6-dimethoxy-7-methyl-rearrangement, 5, 558 Purine, 2,7-dimethyl-halogenation, 5, 547 Purine, 7,9-dimethyl-UV spectra, 5, 517 Purine, 8,8-dimethyl-synthesis, 5, 580 Purine, 6-dimethylamino-mass spectra, 5, 519 occurrence, 5, 600 Purine, 6-dimethylamino-9-benzyl-alkylation, 5, 531 Purine, 3,7-dimethyl-6,8-dioxo-methylation, 5, 534 Purine, 6,8-dioxo-alkylation, 5, 534... 

C22H34N12O10Pt2+-1.5 Cl- 0.5 I--2 H20 ranosyl]-6-(dimethylamino)purine, dihydrochloride, pentahydrate (puromycin, dihydrochloride, pentahydrate) Ethylenediamine-bis(guanosine) platinum(II), chloride, EGUOSP 34 375... 

Synthetic Studies. V. 6-Dimethylamino-9-(2 -acetamino-/ -D-glucopyrano-syl)-purine. J. org. Chemistry 19, 1786 (1954). 

Dimethylamino-9-(3/-amino-3,-deoxy-D-ribofuranosyl)-purine. J. Amer. chem. Soc. 77, 2396 (1955). 

Treatment of 1-methyl-4-cyano-5-aminoimidazole with phosgeniminium chloride produced an imidazoloamidine (64% yield) that cyclized when exposed to dry hydrogen chloride gas (95% yield) to give 6-chloro-2-dimethylamino-9-methylpurine <1997T8269>. Elaboration of this material led to the first synthesis of the natural product purine heteromine A (see Section 10.11.12.1). 

Triazenes and related compounds. A complex of thorium tetranitrate with 2,4,6-tris(dimethylamino)triazene (C9H18N6, hexamethylmelamine), Th(N03)4-C9Hi8N6, and the probably polymeric derivatives of purine and adenine, Th(CsH3N4)2Cl2, have been recorded,43 but little is known about them. 

Dimethylaminopropionitrile, AE66 6-(Dimethylamino)purine, AK97 Dimethylammonium chloride, A 07... 

Figure 4. MECC chromatogram of the purines adenine(A), 6-methylpurine(B), 2 hydroxypurine(C), 6,6-dimethylamino-purine(D), and xanthine(E).

Note Despite the large variety in substituents in the pyrimidine ring, dimethylamino (+1), chloro (-1) and oxo (-M), the respective purine-8-ylidene ligands were remarkably similar in their electronic properties (A vCO of cm- ) [102],... 

Information on tautomerism, and sites of protonation of purines has been derived from NMR spectral studies. Thus protonation of adenine is first suggested to occur at N-1 with no evidence for protonation of the amino group (65JOC1110) although protonation of the substituted amino group does occur in 6-dimethylamino-3-methylpurine (68CC1002). 

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). 

Dimethylamino-9-[(3-p-methoxy-/3- l.-phenylalanylamino)-3-deoxy-/3-D- ribofuranosyl]purine 3 -Deoxyadenosine Puromycin (5. alboniger) B-70MI40900, p. 13... 

Thus, uracil 223 is converted by N-phenylphosphoric acid triamide in 46% yield into 2,4-bis-phenylaminopyrimidine (224), whereas HMPA aminates uracil 223 to the 2,4-bis-dimethylaminopyrimidine (225) in 78% yield (70IZV904). The amination of xanthine 226 by HMPA furnishes 79% of 2,6-bis-(dimethylamino)purine (227) (701ZV953). 

It was shown that the 2-methylsulfanyl group of 2-(methylsulfanyl)adenine could not be replaced successfully by ammonia under a variety of conditions and this experience was duplicated using allcylamines." However, in the case of 2-(methylsulfanyl)purin-6-ol it is possible to perform the displacement reaction in alcoholic amine solution to give, for example, the 2-dimethylamino derivative 3. ... 

Dimethylamino)-9-( -D-ribofuranosyl)purin-6-ol (A, A -Dimethylguanosine, 9) Typical Procedure ... 

Monaharan has developed a versatile synthetic route for the synthesis of 2 -0-[(N, iV-dimethylamino)-oxyethyl] modified purine and pyrimidine nucleoside phosphoramidites (63a-d) to be used as antisense oligonucleotide building blocks. In the syntheses of the purine-based analogues, the (iV, N-dimethylamino)-oxyethyl group was introduced via a 2 -allyloxy nucleoside intermediate, while the pyrimidine-based nucleosides were obtained from the TBDMS-protected 2,2 -anhydro-5-methyluridine via ring opening reaction in the presence of borane and ethylene glycol. The aminoxy derivatives were... 

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... 

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