1928-77-4

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-7-BENZYLPURINE is used as a key intermediate for the synthesis of 1-substituted adenines, which are essential components in the development of various pharmaceutical products. Its role in the synthesis process is crucial for creating new and innovative medications that can address a wide range of health concerns.
Used in Chemical Synthesis:
In the field of chemical synthesis, 6-CHLORO-7-BENZYLPURINE is utilized as an important building block for creating a variety of complex organic molecules. Its unique structure and reactivity make it a valuable asset in the development of new compounds with diverse applications, including but not limited to, materials science, agrochemicals, and specialty chemicals.
Used in Research and Development:
6-CHLORO-7-BENZYLPURINE is also employed in research and development settings, where it is used to explore new chemical reactions and pathways. Its versatility as a synthetic intermediate allows researchers to investigate novel approaches to drug discovery and the creation of advanced materials with improved properties.

InChI:InChI=1/C12H9ClN4/c13-11-10-12(15-7-14-11)16-8-17(10)6-9-4-2-1-3-5-9/h1-5,7-8H,6H2

Upstream product

• 87-42-3 6-chloropurine 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 
• 87-42-3 6-chloro-7H-purine 
• 3724-43-4 Vilsmeier reagent 
• 100-39-0 benzyl bromide 
• 1258274-72-4 6-chloro-7,8-dihydro-9-tritylpurine 
• 1374867-86-3 9-tert-butoxycarbonyl-7-benzyl-6-chloro-7,8-dihydropurine 
• 1374867-77-2 9-tert-butoxycarbonyl-6-chloro-7,8-dihydropurine 
• 851165-38-3 9-tert-butoxycarbonyl-6-chloro-9H-purine 
• 1008361-76-9 6-chloro-9-trityl-9H-purine 

Downstream Products

• 18346-06-0 7-benzyl-7H-purine 
• 129942-19-4 7-benzyl-6-(isopropylamino)purine 
• 4059-08-9 N⁶,7-dibenzyladenine 
• 150721-88-3 7-benzyl-6-iodo-7H-purine 
• 3691-50-7 7-benzyladenine 
• 1431332-82-9 7-benzyl-N-(triphenylphosphoranylidene)purine-6-amine 

Relevant academic research and scientific papers

Regioselective alkylation reaction of purines under microwave irradiation

The alkylation of purines which is generally carried out after anion formation by treatment with a base and alkyl halide is complicated and in the best cases, mixtures of N-alkylated compounds are obtained. Purine derivatives can be acquired from alkylati

Iodine-catalyzed oxidative functionalization of purines with (thio)ethers or methylarenes for the synthesis of purin-8-one analogues

An efficient oxidative functionalization of purine-like substrates with (thio)ethers or methylarenes under mild conditions is described. Using I2as the catalyst, and TBHP as the oxidant, this protocol provides a valuable synthetic tool for the assembly of a wide range of 9-alkyl(benzyl)purin-8-one derivatives with high atom- and step-economy and exceptional functional group tolerance.

METHOD FOR SYNTHESIZING DIVERSELY SUBSTITUTED PURINES

The present invention relates to a method for synthesizing diversely substituted purines starting from a pyrimidine. Formula (I). The method comprises the formation of an amidine group on the pyrimidine by implementing a Vilsmeier type reagent, the functi

A One-Pot Synthesis of Highly Functionalized Purines

Highly substituted purines were synthesized in good to high yields through a one-pot straightforward metal-free scalable method, using the Traube synthesis adapted to Vilsmeier-type reagents. From 5-amino-4-chloropyrimidines, new 9-aryl-substituted chloropurines and intermediates for peptide nucleic acid synthesis were prepared. Variant procedures allowing a rapid synthesis of ribonucleosides and 7-benzylpurine from 5-amidino-6-aminopyrimidines are also reported to illustrate the high potential of this versatile toolbox. This route appears to be particularly interesting in the field of nucleic acids for a direct and rapid access to various new 8-alkylpurine nucleosides.

Direct, Regioselective N-Alkylation of 1,3-Azoles

Regioselective N-alkylation of 1,3-azoles is a valuable transformation. Organomagnesium reagents were discovered to be competent bases to affect regioselective alkylation of various 1,3-azoles. Counterintuitively, substitution selectively occurred at the more sterically hindered nitrogen atom. Numerous examples are provided, on varying 1,3-azole scaffolds, with yields ranging from 25 to 95%.

Regioselective and facile synthesis of 7,9-dialkyl-8-oxopurines from 7,9-dialkyl-7,8-dihydropurines: Total synthesis of heteromines i and J

A novel protocol for the synthesis of 6-halo-8-oxo-7,8-dihydro-9H-purines based on the oxidation of 7,9-dialkyl-7,8-dihydro-9H-purines has been developed. The presented methodology was used as a key step in the synthesis of heteromines I and J. Georg Thie

Highly efficient and broad-scope protocol for the preparation of 7-substituted 6-halopurines via N 9-Boc-protected 7,8-dihydropurines

9-Boc-6-chloropurine, which can be obtained in high yield, is nearly quantitatively reduced with the THFBH3 complex. The obtained 9-Boc-7,8-dihydropurine derivative is more stable compared to the corresponding 9-tritylpurine and can be smoothly

Selective synthesis of 7-substituted purines via 7,8-dihydropurines

A simple and efficient protocol for the preparation of 7-substituted purines is described. 6- and 2,6-Dihalopurines were N9-tritylated and then transformed to 7,8-dihydropurines by DIBAL-H. Subsequent N 7-alkylation followed by N9-trityl deprotection with trifluoroacetic acid was accompanied by spontaneous reoxidation, which led to the 7-substituted purines at 55 - 88% overall isolated yields.

Synthesis and biological testing of purine derivatives as potential ATP-competitive kinase inhibitors

On the basis of ATP adenine, a series of adenine and purine derivatives was prepared and tested for their ability to inhibit a spectrum of disease-related kinases. There has been scant research investigating the potential of cosubstrate derived kinase inhibitors for other kinases than CDKs. Our inhibitor design combined the purine system from the original cosubstrate ATP and phenyl moieties in order to explore possible interactions with the different regions of the ATP binding site in several disease-related protein kinases. There have been a number of hits for the assayed substances, which led us to conclude that the spectrum of compounds may prove to be a valuable tool kit for the evaluation of bonding and selectivity patterns for a wide variety of kinases.

Design, synthesis and structure-activity relationships of a series of 9-substituted adenine derivatives as selective phosphodiesterase type-4 inhibitors

Adenine derivatives substituted in position 9 have been demonstrated to have potent cyclic nucleotide phosphodiesterase (PDE) inhibition properties with high selectivity toward PDE-4. Starting from our initial lead compound 9-(2-fluorobenzyl)-N6-methyl-2-trifluoromethyladenine (4, NCS613), we designed and synthesized a new series of 9-substituted derivatives for developing structure-activity relationship studies. This new series of derivatives showed increased potencies and better selectivity profiles. Structural modifications were achieved in parallel on three different positions of the adenine ring, and led to the following observations: (i) introduction of a lipophilic substituent such as trifluoromethyl, n-propyl group or iodine in the C-2 position is favourable for both the PDE-4 inhibitory activity and the selectivity towards other isoenzymes; (ii) functionalization of the N9 benzyl group with a 2-methoxy substituent led to remarkably more active compounds; (iii) replacement of the N6-methylamino moiety by other amino groups is detrimental to the activity. Among all derivatives prepared, the 9-(2-methoxybenzyl)-N6-methyl-2-trifluoromethyladenine (9r), 9-(2-methoxybenzyl)-N6-methyl-2-n-propyladenine (9s), and the 2-iodo-9-(2-methoxybenzyl)-N6-methyladenine (13b) were found to be the most potent inhibitors within this series (PDE-4-IC50=1.4, 7.0, and 0.096 nM, respectively). Compared to our reference compound 4, which showed an IC50 of 42 nM, the derivative 13b was found 450-fold more potent. Moreover, 2-iodo-9-(2-methoxybenzyl)-N6-methyladenine (13b) and 9-(2-methoxybenzyl)-N6-methyl-2-trifluoromethyladenine (9r), were at least 50 000-150 000 times more selective for the PDE-4 than for the other PDE families. Additionally, these new derivatives showed improved efficiency in inhibiting the TNFα release from mononuclear cells from healthy subjects (e.g. adenines 7l, 9s and 13b). Thus, compounds 7l, 9r, 9s and 13b are among the most potent and selective PDE-4 inhibitors reported so far and represent very promising pharmacological tools for a better understanding of the signal transduction involving cyclic AMP within the cell: this pathway is implicated in the physiology and the pathophysiology of inflammation, asthma and autoimmune disorders.