83135-02-8

Basic information

• Product Name: 9H-Purine, 6-phenyl-9-(phenylmethyl)-
• CAS NO: 83135-02-8
• Molecular Formula: C18H14N4
• Molecular Weight: 286.336
• Mol File: 83135-02-8.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 9H-Purine, 6-phenyl-9-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Purine, 6-phenyl-9-(phenylmethyl)-(83135-02-8)
• EPA Substance Registry System: 9H-Purine, 6-phenyl-9-(phenylmethyl)-(83135-02-8)

Safety Data

• Hazardous Substances Data: 83135-02-8(Hazardous Substances Data)

Upstream product

• 25491-56-9 9-benzyl-9H-purine 
• 98-80-6 phenylboronic acid 
• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 83135-13-1 9-benzyl-6-iodo-9H-purine 
• 960-16-7 tributylphenylstannane 
• 87-42-3 6-chloropurine 
• 100-44-7 benzyl chloride 
• 24344-61-4 1,3-bis-(tri-n-butylstannyl)benzene 
• 17151-51-8 1,4-bis-(tri-n-butylstannyl)benzene 
• 1012-73-3 1,4-bis(trimethylstannyl)benzene 
• 4612-26-4 1,4-Phenyldiboronic acid 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 4261-14-7 9-benzyl-9H-purin-6-ylamine 

Downstream Products

• 1284287-13-3 6-([1,1′-biphenyl]-2-yl)-9-benzyl-9H-purine 

Relevant articles and documents

Covalent analogues of DNA base-pairs and triplets. Part 3: Synthesis of 1,4- and 1,3-bis(purin-6-yl)benzenes and 1-(1,3-dimethyluracil-5-yl)-3 or 4-(purin-9-yl)benzenes

The Stille cross-coupling reactions of 1,4- and 1,3-bis(trialkylstannyl)benzenes 2 or 3 with 9-benzyl-6-chloropurine (1) led either to mono-coupled 4- or 3-[(tributylstannyl)phenyl]benzenes 5a and 5b or to bis(9-benzylpurin-6-yl)benzenes (4a or 4b) depending on the ratio of the starting compounds, nature of the stannane and conditions. Analogous reaction of 1 with benzene-1,4-diboronic acid gave selectively 4a in good yield. The reaction of stannanes 5 with 1,3-dimethyl-5-iodouracil gave 1-(9-benzylpurin-6-yl)-4- or -3-(1,3-dimethyluracil-5-yl)benzenes (10a and 10b) in low yields. Compounds 4 and 10 are novel types of covalently linked analogues of nucleobase-pairs.

Silver-Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids

A practical and operationally simple protocol for the assembly of 6-aryl-substituted purines through the direct C6–H arylation of purines and 8-azapurine and purine nucleosides from arylboronic acids was developed. This reaction was performed under ambient conditions with ammonium persulfate as the oxidant in the presence of silver(I). The reaction was found to be regioselective with the arylation occurring predominantly at the C6 position, and a large variety of functional groups, including halides, esters, hydroxy groups, and heterocycles, were tolerated.

Rhodium-catalyzed intermolecular amidation of arenes with sulfonyl azides via chelation-assisted C-H bond activation

We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N2 as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue to practical intermolecular C-N bond formation.