Thiamiprine

Base Information

• Chemical Name: Thiamiprine
• CAS No.: 5581-52-2
• Deprecated CAS: 33222-63-8
• Molecular Formula: C9H8 N8 O2 S
• Molecular Weight: 292.281
• Hs Code.: 2933990090
• European Community (EC) Number: 226-977-5
• NSC Number: 38887
• UNII: E2EV7ZDD1M
• DSSTox Substance ID: DTXSID70204396
• Nikkaji Number: J9.555I
• Wikidata: Q27276780
• NCI Thesaurus Code: C1251
• ChEMBL ID: CHEMBL34722
• Mol file: 5581-52-2.mol

Synonyms:6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-1H-purin-2-amine;BW 57-323;BW-57-323;Guaneran;thiamiprine

Chemical Property of Thiamiprine

Chemical Property:

• Vapor Pressure: 2.45E-14mmHg at 25°C
• Melting Point: >200℃ (DEC.)
• Refractive Index: 1.7400 (estimate)
• Boiling Point: 599.6°Cat760mmHg
• PKA: 6.66±0.20(Predicted)
• Flash Point: 316.4°C
• PSA: 169.42000
• Density: 2.05g/cm³
• LogP: 1.83240
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 292.04909270
• Heavy Atom Count: 20
• Complexity: 381

Purity/Quality:

99% ^*data from raw suppliers

Thiamiprine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=NC(=C1SC2=NC(=NC3=C2NC=N3)N)[N+](=O)[O-]
• Uses: An immunosuppressant. Antiarthritic.

Technology Process of Thiamiprine

There total 2 articles about Thiamiprine 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: 87.0%

thioguanine (154-42-7) + 5-chloro-1-methyl-4-nitroimidazole (4897-25-0) → 2-amino-6<(1-methyl-4-nitroimidazol-5-yl)-thio>purine (5581-52-2)

Guidance literature:

With sodium hydroxide; for 4h; Heating;

DOI:10.1007/BF02283549

Reference yield:

→ 2-amino-6<(1-methyl-4-nitroimidazol-5-yl)-thio>purine (5581-52-2)

Guidance literature:

6-Thioguanin(Ib),1-Methyl-4-nitro-5-chlor-imidazol;

Reference yield: 69.0%

2-amino-6<(1-methyl-4-nitroimidazol-5-yl)-thio>purine (5581-52-2) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → Thiamiprine 2'-deoxyriboside (61552-42-9,61552-41-8)

Guidance literature:

With dipotassium hydrogenphosphate; potassium dihydrogenphosphate; potassium acetate; In 1,2-dimethoxyethane; water; dimethyl sulfoxide; thymidine phosphorylase, purine nucleoside phosphorylase; 1) 24 deg C, 1 h, 2) 35 deg C, 17 h;

DOI:10.1021/jm00127a013

upstream raw materials:

thioguanine

5-chloro-1-methyl-4-nitroimidazole

Downstream raw materials:

Thiamiprine riboside

Thiamiprine 2'-deoxyriboside