20145-09-9

Upstream product

• 5470-24-6 6-Chloro-9-phenyl-9H-purine 
• 41259-65-8 6-chloro-N₄-phenylpyrimidine-4,5-diamine 
• 108-95-2 phenol 
• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 66224-66-6 adenine 
• 66950-63-8 phenyl N,N-dimethylsulfamate 
• 591-50-4 iodobenzene 
• 1167987-42-9 8-bromo-9-phenyladenine 
• 28856-55-5 N⁶-(N,N-dimethylaminomethylidene)adenine 
• 98-80-6 phenylboronic acid 
• 127820-31-9 N⁴-phenyl-pyrimidine-4,5,6-triyltriamine; sulfate 
• 77287-34-4 formamide 

Downstream Products

• 1427272-57-8 8-chloro-9-phenyl-9H-purin-6-amine 
• 6334-42-5 1,9-dihydro-9-phenyl-6H-purin-6-one 

Relevant academic research and scientific papers

Copper-catalyzed cross-coupling reactions of nucleobases with arylboronic acids: An efficient access to N-arylnucleobases

An efficient avenue for the direct N-arylation of nucleobases with arylboronic acids that is catalyzed by simple copper salts was discovered. The N-arylnucleobases were obtained in excellent yields at room temperature within 45 min when methanol and water

N -Arylation of (hetero)arylamines using aryl sulfamates and carbamates via C-O bond activation enabled by a reusable and durable nickel(0) catalyst

An effective and general aryl amination protocol has been developed using a magnetically recoverable Ni(0) based nanocatalyst. This new stable catalyst was prepared on Fe3O4@SiO2 modified by EDTA and investigated by FT-IR, EDX, TEM, XRD, DLS, FE-SEM, XPS, NMR, TGA, VSM, ICP and elemental analysis techniques. The reaction proceeded via carbon-oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles with good to excellent yields. Furthermore, the catalyst could be easily recovered by using an external magnetic field and directly reused at least six times without notable reduction in its activity. This journal is

Direct N9-arylation of purines with aryl halides

An efficient method for N-arylation of purines is reported. The N-arylation is catalysed by Cu(i) and 4,7-bis(2-hydroxyethylamino)-1,10-phenanthroline (BHPhen) in aqueous DMF or ethanol. The reaction generally proceeds with high selectivity for the N

Synthetic strategies to 9-substituted 8-oxoadenines

Three synthetic routes to 9-substituted 8-oxoadenines have been studied: bromination of adenine followed by N-9-alkylation/arylation and finally hydrolysis; bromination of adenine, hydrolysis, and N-functionalization as the last step; and N-9-alkylation of adenine, halogenation, and finally hydrolysis. As long as the N-9-functional group is compatible with conditions required for introduction of the halogen, the latter strategy was the most efficient. Also, a strategy starting from 5-amino-4,6-dichloropyrimidine was found to be a very good alternative for synthesis of 9-substituted 8-oxoadenines. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Selective copper catalysed aromatic N-arylation in water

4,7-Dipyrrolidinyl-1,10-phenanthroline (DPPhen) was identified as an efficient ligand for copper catalysed selective aromatic N-arylation in water. N-Arylation of indoles, imidazoles and purines proceeds with moderate to excellent yields and complete selectivity over aliphatic amines. Aqueous medium and the possibility for low metal and ligand loadings give the process a benign environmental profile.

New Approach to the Synthesis of N7-Arylguanines and N 7-Aryladenlnes

The copper-mediated arylation of 7-methylpyrimido[1, 2-α]- purin-10(3H)-one (1) in dichloromethane or of N7- (climethylaminojmethyleneguanine (2) in methanol in the presence of TMEDA as a base/ligand led to the preferential formation of l-aryl-

Copper-mediated N-arylation in the synthesis of aryladenines

A series of N3 and N9 aryladenines was prepared by arylation of 8-bromoadenine under modified Chan-Lam-Evans coupling conditions followed by reductive debromination with hydrogen on palladium. Conditions of arylation were optimised to maximise the yield o

A mild and efficient method for N-arylnucleobase synthesis via the cross-coupling reactions of nucleobases with arylboronic acids catalyzed by simple copper salts

A simple and efficient copper-salt catalyzed N-arylation of nucleobases is reported. In a mixed solvent of MeOH and H2O, the coupling products were obtained in moderate to excellent yields at room temperature within a short time. Avariety of su

N6,9-Disubstituted Adenines: Potent, Selective Antagonists at the A1 Adenosine Receptor

N6-Substituted 9-methyladenines are potent antagonists of the activation of A1 adenosine receptors.The present study assessed the effect of N6 and N-9-substituents on the binding of adenines to the A1 and A2 receptors, respectively, of rat brain cortex and striatum and also on the antagonism of the A2 receptor mediated stimulation of the adenylate cyclase of PC12 cells by N-ethyladenosine-5'-uronamide.The potency ranking of 9-substituted adenines varied directly with the hydrophobicity of the substituent: cyclopentyl > phenyl > tetrahydrofuryl > ethyl > methyl > 2-hydroxyethyl.The 9-substituted adenines showed little selectivity for either receptor and the R enantiomer of N6-(1-phenyl-2-propyl)-9-methyladenine was only 4-fold more potent than the S enantiomer at the A1 receptor.An N6-cyclopentyl substituent increased potency at the A1 receptor and decreased potency at the A2 receptor, resulting in selectivity for the A1 receptor of up to 39-fold.The N6-cyclopentyl group completely overshadowed the effect of the hydrophobicity of the 9-substituent.A 2-chloro substituent did not alter the potency of an N6-substituted 9-methyladenine.