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

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

• 4261-14-7 9-benzyl-9H-purin-6-ylamine 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 960-16-7 tributylphenylstannane 
• 591-50-4 iodobenzene 
• 83135-13-1 9-benzyl-6-iodo-9H-purine 
• 98-80-6 phenylboronic acid 
• 4612-26-4 1,4-Phenyldiboronic acid 
• 1012-73-3 1,4-bis(trimethylstannyl)benzene 
• 25491-56-9 9-benzyl-9H-purine 
• 87-42-3 6-chloropurine 
• 100-44-7 benzyl chloride 
• 24344-61-4 1,3-bis-(tri-n-butylstannyl)benzene 

Downstream Products

• 1447307-84-7 2-(9-benzyl-9H-purin-6-yl)phenol 
• 1447307-95-0 2-(9-benzyl-9H-purin-6-yl)-1,3-phenylene diacetate 
• 1310063-70-7 acetic acid 2-(9-benzyl-9H-purin-6-yl)-phenyl ester 

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.

PdII-Catalyzed Purine-Directed Ortho Nitration of 6-Arylpurines by C(sp2)–H Activation: A Practical Approach to Synthesize 6-(2-Nitroaryl)-Purine Derivatives

Herein we report a method for PdII-catalyzed purine-directed ortho nitration of 6-arylpurines via C(sp2)–H activation by using tBuONO/O2 as nitration agent. This procedure is highly efficient and produces a range of 6-(2-nitroaryl)-purine derivatives with good chemoselectivity and functional-group tolerance. The utility of the method is further illustrated in the synthesis of antibacterial agent.

Visible-Light-Mediated Monoselective Ortho C-H Arylation of 6-Arylpurine Nucleosides with Diazonium Salts

A combined palladium- and photoredox-catalyzed monoselective arylation of 6-arylpurine nucleosides has been developed by employing purine as a directing group via the photoredox reaction, and many functional groups are well tolerated in this direct C-H arylation condition. Various of functionalized purines (nucleosides) which are potentially of great importance in medicinal chemistry could be obtained under visible light irradiation at room temperature within 4 h.

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.

Microwave promoted palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of 6-chloropurines with sodium tetraarylborate in water

An efficient method for the synthesis of 6-arylpurines (nucleosides) was developed via Suzuki-Miyaura cross-coupling reactions of 6-chloropurines (nucleosides) and sodium tetraarylborate in neat water (ethanol). The process gave good to high isolated yiel

Cross-coupling reactions of halopurines with aryl- and alkyltrifluoroborates; the scope and limitations in the synthesis of modified purines

The scope and limitations of the use of the palladium-catalyzed cross-coupling reactions of diverse alkyl- and aryltrifluoroborates with halopurines have been studied. While aryl- and hetaryltrifluoroborates reacted readily with both 6-chloropurines and 8

Reductive dimerization of 2- and 6-iodopurines: Side reaction in Pd-catalyzed cross-coupling of iodopurines

In the presence of a Pd catalyst and a base, 6- and 2-iodopurine derivatives undergo reductive C-C dimerization with the formation of the corresponding 6,6′- or 2,2′-dimers. The best results of the dimerization were obtained in the presence of i-Pr2

Isonitriles as efficient ligands in Suzuki-Miyaura reaction

Isonitrile palladium complexes [(RNC)2PdCl2] were prepared and tested in Suzuki reaction of 4-chloroanisol. (AdNC)2PdCl2 was found the most effective catalyst and was used in phenylation of several chloro and bromoaromatic substrates.

The Suzuki-Miyaura cross-coupling reactions of 2-, 6- or 8-halopurines with boronic acids leading to 2-, 6- or 8-aryl- and -alkenylpurine derivatives

The Suzuki-Miyaura cross-coupling reactions of 9-benzyl-6-chloropurine, 9- or 3-benzyl-8-bromoadenine and 2,6-dihalopurines with boronic acids gave the corresponding 6-, 8- or 2-aryl- or -alkenylpurines in good yields. Anhydrous conditions in toluene were