6-Methylmercaptopurine

Base Information

• Chemical Name: 6-Methylmercaptopurine
• CAS No.: 50-66-8
• Molecular Formula: C6H6N4S
• Molecular Weight: 166.206
• Hs Code.: 29335995
• European Community (EC) Number: 200-057-3
• NSC Number: 20105
• UNII: 6V404DV25O
• DSSTox Substance ID: DTXSID50901654
• Nikkaji Number: J79.423F
• Wikidata: Q27103606
• Metabolomics Workbench ID: 51654
• ChEMBL ID: CHEMBL1178
• Mol file: 50-66-8.mol

Synonyms:6-methylmercaptopurine;6-methylthiopurine;methylmercaptopurine

Chemical Property of 6-Methylmercaptopurine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.00351mmHg at 25°C
• Melting Point: 219-223 °C
• Refractive Index: 1.806
• Boiling Point: 470.2 °C at 760 mmHg
• Flash Point: 238.2 °C
• PSA: 79.76000
• Density: 1.47 g/cm³
• LogP: 1.07480
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in water (769 mg/L).
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 166.03131738
• Heavy Atom Count: 11
• Complexity: 143

Purity/Quality:

99% ^*data from raw suppliers

6-Methylmercaptopurine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CSC1=NC=NC2=C1NC=N2
• Uses: 6-(Methylthio)purine is an immunosuppressive drug used to treat leukemia.

Technology Process of 6-Methylmercaptopurine

There total 14 articles about 6-Methylmercaptopurine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

6-chloropurine (87-42-3) + sodium thiomethoxide (5188-07-8) → 6-methylthiopurine (50-66-8)

Guidance literature:

In N,N-dimethyl-formamide; at 80 ℃; for 0.0166667h; microwave irradiation;

DOI:10.1016/j.tet.2007.02.124

Reference yield: 93.0%

boron dimethyl-trifluoro sulphide (353-43-5) + 6-chloro-7H-purine (87-42-3,111055-92-6) → 6-(methylthio)-1H-purine (50-66-8)

Guidance literature:

In neat (no solvent); at 60 ℃; for 16h; Sealed tube;

DOI:10.1002/ejoc.201900503

Reference yield: 69.0%

6-Mercaptopurine (157930-09-1,157930-10-4,157930-11-5,157930-13-7,157930-14-8) + methyl iodide (74-88-4) → 6-methylthiopurine (50-66-8)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 12h;

DOI:10.1007/s11094-021-02369-1

upstream raw materials:

6H-purine-6-thione

2,6,8-trichloro-7H-purine

8-chloroxanthine

1,7-dihydro-6H-purin-6-one

Downstream raw materials:

kinetin

[2-(1⁽³⁾H-imidazol-4-yl)-ethyl]-(7⁽⁹⁾H-purin-6-yl)-amine

6-methylsulfanyl-9-tetrahydropyran-2-yl-9H-purine

6-(methylthio)-9-(tetrahydrofuran-2-yl)-9H-purine

Refernces

• 1、 Hu, Rong,Wang, Wan-Li,Xiao, Kun-Jie,Wang, Ning-Yu. "9-Sulfonyl-9(H)-Purine Derivatives Inhibit HCV Replication Via their Degradation Species". . p. 36 - 45. Retrieved 2021/04/19.
• 2、 S?derstr?m, Marcus,Zamaratski, Edouard,Odell, Luke R.. "BF3·SMe2 for Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles". . p. 5402 - 5408. Retrieved 2019/06/27.