5440-17-5

Basic information

• Product Name: 6-CHLORO-7-METHYLPURINE
• Synonyms: 6-CHLORO-7-METHYLPURINE;7-METHYL-6-CHLOROPURINE;NSC 15192;6-Chloro-7-methyl-7H-purine
• CAS NO: 5440-17-5
• Molecular Formula: C₆H₅ClN₄
• Molecular Weight: 168.58
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 5440-17-5.mol

Chemical Properties

• Melting Point: 175-185°C
• Boiling Point: 321.7 °C at 760 mmHg
• Flash Point: 148.4 °C
• Appearance: light green solid
• Density: 1.59 g/cm³
• Vapor Pressure: 0.000293mmHg at 25°C
• Refractive Index: 1.743
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
• PKA: 0.65±0.30(Predicted)
• CAS DataBase Reference: 6-CHLORO-7-METHYLPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-7-METHYLPURINE(5440-17-5)
• EPA Substance Registry System: 6-CHLORO-7-METHYLPURINE(5440-17-5)

Safety Data

• Hazardous Substances Data: 5440-17-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-7-METHYLPURINE is used as a synthetic intermediate for the development of various pharmaceutical products. Its unique chemical structure allows it to be a key component in the synthesis of drugs targeting specific medical conditions.
Used in Chemical Synthesis:
6-CHLORO-7-METHYLPURINE is also used as a synthetic intermediate in the chemical industry for the production of different compounds. Its versatility in chemical reactions makes it a valuable asset in creating a wide range of products.

InChI:InChI=1/C6H5ClN4/c1-11-3-10-6-4(11)5(7)8-2-9-6/h2-3H,1H3

Upstream product

• 87-42-3 6-chloropurine 
• 74-88-4 methyl iodide 
• 110475-17-7 5-amino-3-methyl-3H-imidazole-4-carboxylic acid amide; hydrochloride 
• 74-87-3 methylene chloride 
• 32916-51-1 cyclopentylmagnesium chloride 
• 87-42-3 6-chloro-7H-purine 
• 1374867-82-9 9-tert-butoxycarbonyl-6-chloro-7,8-dihydro-7-methylpurine 
• 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 
• 1258274-87-1 6-chloro-7,8-dihydro-7-methyl-9-tritylpurine 
• 1258274-72-4 6-chloro-7,8-dihydro-9-tritylpurine 
• 67-56-1 methanol 
• 1006-08-2 7-methyl-1,7-dihydro-purin-6-one 

Downstream Products

• 38917-24-7 6-methoxy-7-methyl-7H-purine 
• 108871-28-9 (4-chloro-phenyl)-(7-methyl-7H-purin-6-yl)-amine; hydrochloride 
• 5444-56-4 6-(4-chloro-phenoxy)-7-methyl-7H-purine 
• 3324-79-6 7-Methyl-6-thiopurin 
• 104997-53-7 (4-bromo-phenyl)-(7-methyl-7H-purin-6-yl)-amine 
• 935-69-3 7-methyladenine 
• 455267-79-5 (7-Methyl-7H-purin-6-yl)-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-ylmethyl]-amine 
• 1229593-31-0 6-(2-hydroxy-3-methylbenzylamino)-7-methylpurine 
• 3324-79-6 7-methyl-6-mercaptopurine 
• 1006-08-2 7-methyl-1,7-dihydro-purin-6-one 
• 1008-01-1 7-methyl-6-(methylthio)-7H-purine 

Relevant articles and documents

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

OXADIAZOLE TRANSIENT RECEPTOR POTENTIAL CHANNEL INHIBITORS

The invention relates to compounds of formula I: and pharmaceutically acceptable salts thereof wherein A, X, R1, R4 and n are as defined herein. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

6-Substituted purines as ROCK inhibitors with anti-metastatic activity

Rho-associated serine/threonine kinases (ROCKs) are principal regulators of the actin cytoskeleton that regulate the contractility, shape, motility, and invasion of cells. We explored the relationships between structure and anti-ROCK2 activity in a group

ECTONUCLEOTIDE PYROPHOSPHATASE-PHOSPHODIESTERASE 1 (ENPP-1) INHIBITORS AND USES THEREOF

Disclosed herein are methods and compounds of augmenting and enhancing the production of type I IFNs in vivo. In some embodiments, the compounds disclosed herein are ENPP-1 inhibitors, pharmaceutical compositions, and methods for the treatment of cancer or a viral infection.

OXADIAZOLONES AS TRANSIENT RECEPTOR POTENTIAL CHANNEL INHIBITORS

The invention relates to compounds of formula (I) and pharmaceutically acceptable salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula (I) as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

Mechanism of Action of the Cytotoxic Asmarine Alkaloids

The asmarines are a family of cytotoxic natural products whose mechanism of action is unknown. Here, we used chemical synthesis to reverse engineer the asmarines and understand the functions of their individual components. We found that the potent asmarine analog delmarine arrested the mammalian cell cycle in the G1 phase and that both cell cycle arrest and cytotoxicity were rescued by cotreatment with ferric and ferrous salts. Cellular iron deprivation was clearly indicated by changes in iron-responsive protein markers, and cytotoxicity occurred independently of radical oxygen species (ROS) production. Chemical synthesis allowed for annotation of the distinct structural motifs required for these effects, especially the unusual diazepine, which we found enforced an iron-binding tautomer without distortion of the NCNO dihedral angle out of plane. With this information and a correlation of cytotoxicity with logP, we could replace the diazepine by lipophilic group appendage to N9, which avoided steric clash with the N6-alkyl required to access the aminopyridine. This study transformed the asmarines, scarce marine metabolites, into easily synthesized, modular chemotypes that may complement or succeed iron-selective binders in clinical trials and use.

Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds

Alkylation of 4-methoxy-1H-pyrazolo[3,4-d]pyrimidine (1b) with iodomethane in THF using NaHMDS as base selectively provided N2-methyl product 4-methoxy-2-methyl-2H-pyrazolo[3,4-d]pyrimidine (3b) in an 8/1 ratio over N1-methyl product (2b). Interestingly, conducting the reaction in DMSO reversed selectivity to provide a 4/1 ratio of N1/N2 methylated products. Crystal structures of product 3b with N1 and N7 coordinated to sodium indicated a potential role for the latter reinforcing the N2-selectivity. Limits of selectivity were tested with 26 heterocycles which revealed that N7 was a controlling element directing alkylations to favor N2 for pyrazolo- and N3 for imidazo- and triazolo-fused ring heterocycles when conducted in THF. Use of 1H-detected pulsed field gradient-stimulated echo (PFG-STE) NMR defined the molecular weights of ionic reactive complexes. This data and DFT charge distribution calculations suggest close ion pairs (CIPs) or tight ion pairs (TIPs) control alkylation selectivity in THF and solvent-separated ion pairs (SIPs) are the reactive species in DMSO.

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%.

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.