33833-45-3

Basic information

• Product Name: 9-methyl-8-phenyl-9H-purine
• Synonyms: 9-methyl-8-phenyl-9H-purine
• CAS NO: 33833-45-3
• Molecular Weight: 210.238
• Mol File: 33833-45-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9-methyl-8-phenyl-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-methyl-8-phenyl-9H-purine(33833-45-3)
• EPA Substance Registry System: 9-methyl-8-phenyl-9H-purine(33833-45-3)

Safety Data

• Hazardous Substances Data: 33833-45-3(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 20427-22-9 9-methylpurine 
• 77287-34-4 formamide 
• 188710-74-9 5-amino-1-methyl-2-phenylimidazole-4-carbaldehyde 

Relevant articles and documents

DEAMINATION, INVOLVING RING OPENING, IN REACTIONS OF 1-AMINOPURINIUM MESITYLENESULFONATES WITH METHANOLIC AMMONIA

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.

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.