33833-45-3Relevant academic research and scientific papers
DEAMINATION, INVOLVING RING OPENING, IN REACTIONS OF 1-AMINOPURINIUM MESITYLENESULFONATES WITH METHANOLIC AMMONIA
Kos, N. J.,Jongejan, H.,van der Plas, H. C.
, p. 4841 - 4848 (1987)
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.
An Expeditious Procedure for the Synthesis of Purines from Aminoimidazolecarbaldehydes
Perandones, Francisco,Soto, Jose L.
, p. 1459 - 1461 (2007/10/03)
Reactions of 4-amino-1,2-dimelhylimidazole-5-carbaldehyde (1) and 5-amino-1-methylimidazole-4-carbaldehydes 3 with nitriles, in the presence of dry hydrogen chloride afforded to the formation of purine derivatives. This constitutes a facile and versatile one-pot synthesis of purines. The use of formamide instead of nitriles leads to the respective purines without substituents on the pyrimidine ring, 2d and 4e,f.
Anion Formation and Ring Opening of 9-Substituted Purines in Liquid Ammonia Containing Potassium Amide
Kos, Nico J.,Plas, Henk C. van der,Blees, Wouter J. F.
, p. 850 - 855 (2007/10/02)
Reaction of 9-methylpurine, 6-chloro-9-methylpurine, and 2',3'-O-isopropylidenenebularine with potassium amide in liquid ammonia leads to opening of the imidazole ring, yielding, after hydrolysis during the workup, 4-(substituted amino)-5-formamidopyrimidines. 6-Chloro-9-methylpurine gives, besides 6-chloro-4-(methylamino)-5-formamidopyrimidine as main product, small amounts of 9-methyladenine and 6-chloro-7,8-dihydro-8-oxo-9-methylpurine.The ring opening will involve adduct formation at position 8.Nebularine, adenosine, and 2',3'-O-isopropylideneadenosine do not react .With a greater excess of potassium amide 2',3'-O-isopropylideneadenosine loses the sugar moiety.The existence of an anion at position 8 can be proved in 9-methylpurine via scavenging with bromobenzene in liquid ammonia containing potassium amide, yielding the 8-phenyl derivative.With 6-chloro-9-(2-tetrahydropyranyl)purine this reaction gives 6-anilino-9-(2-tetrahydropyranyl)purine.Scavenging of 9-methyladenine with bromobenzene gives 6-anilino-9-methylpurine. 1H and 13C NMR spectroscopy confirm that in this strongly basic medium 7- and 9-methyladenine and 6-(methylamino)-9-methylpurine deprotonate at C-8 and lose a proton from the amino group.Both 8-(methylthio)- and 8-amino-9-methylpurine give with potassium amide in liquid ammonia opening of the imidazole ring, yielding 5-(cyanoamino)-4-(methylamino)pyrimidine, which can react further to give either 8-amino-9-methylpurine or 7,8-dihydro-8-oxo-9-methylpurine.
