84602-83-5

Basic information

• Product Name: N-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine
• Synonyms: N-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine
• CAS NO: 84602-83-5
• Molecular Weight: 295.344
• Mol File: 84602-83-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine(84602-83-5)
• EPA Substance Registry System: N-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine(84602-83-5)

Safety Data

• Hazardous Substances Data: 84602-83-5(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 7306-68-5 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 
• 110-87-2 3,4-dihydro-2H-pyran 
• 1210-66-8 N-phenyl-9H-purin-6-amine 
• 62-53-3 aniline 
• 50-66-8 6-methylthiopurine 
• 19769-32-5 6-methylsulfonylpurine 

Downstream Products

• 1428155-89-8 2-methoxy-N-(3-(6-(phenylamino)-9H-purin-8-yl)phenyl)nicotinamide 
• 1428155-88-7 C₂₄H₁₇FN₆O 
• 1428155-87-6 C₂₅H₂₀N₆O₂ 
• 1428155-75-2 2-methoxy-N-(3-(6-(phenylamino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)phenyl)nicotinamide 
• 1428155-74-1 2-fluoro-N-(3-(6-(phenylamino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)phenyl)benzamide 
• 1428155-73-0 2-methoxy-N-(3-(6-(phenylamino)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)phenyl)benzamide 
• 1428155-69-4 8-(3-aminophenyl)-N-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine 
• 1428155-65-0 8-iodo-N-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine 

Relevant articles and documents

Inhibitors of the TAM subfamily of tyrosine kinases: Synthesis and biological evaluation

The TAM subfamily of Receptor Tyrosine Kinases (RTKs) contains three human proteins of therapeutical interest, Axl, Mer, and Tyro3. Our goal was to design a type II inhibitor specific for this family, i.e. able to interact with the allosteric pocket and with the hinge region of the kinase. We report the synthesis of several series of purine analogues of BMS-777607. The structural diversity of the designed inhibitors was expected to modify the interactions formed in the binding site and consequently to modulate their selectivity profiles. The most potent inhibitor 6g exhibits Kds of 39, 42, 65 and 200 nM against Axl, Mer, Met and Tyro3 respectively. Analysis of the affinity of 6g for active and inactive forms of Abl1, an RTK protein that does not belong to the TAM subfamily, together with the binding modes of 6g predicted by docking studies, indicates that 6g displays some selectivity for the TAM family and may act as a type II inhibitor. Crown Copyright

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.