84602-79-9

Usage

Molecular Weight

194.581 \, \textg/mol
Chlorine atom (Cl) attached to the purine ring
Methyl group (CH3) attached to the purine ring
Oxo group (=O) at the 8th position of the purine ring

Synthetic Analog

Synthetic analog of inosine (purine base)

Function

Selective inhibitor of adenosine deaminase

Biological Activity

Studied for potential antiviral and anticancer properties

Source

Not naturally found in living organisms

Production

Synthesized in the laboratory for scientific studies

Upstream product

• 2346-74-9 6-chloro-9-methyl-9H-purine 
• 52602-68-3 6-chloro-N⁴-methylpyrimidine-4,5-diamine 
• 57-13-6 urea 

Relevant academic research and scientific papers

Preparatory study for the synthesis of the marine sponge alkaloids asmarines A-F: Synthesis of their heterocyclic portions

A synthesis of three tricyclic compounds (1c), (2c), and (3c), selected as models for the heterocyclic portions of the marine sponge alkaloids asmarines A-F, has been accomplished through cyclization of the 7-alkyl-6-chloropurine derivatives.

Anion Formation and Ring Opening of 9-Substituted Purines in Liquid Ammonia Containing Potassium Amide

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.