6-Cyanopurine

Base Information

• Chemical Name: 6-Cyanopurine
• CAS No.: 2036-13-7
• Molecular Formula: C6H3N5
• Molecular Weight: 145.123
• Hs Code.: 2933990090
• European Community (EC) Number: 218-005-3
• NSC Number: 21625
• UNII: XNA156H82X
• DSSTox Substance ID: DTXSID90174284
• Nikkaji Number: J277.585I
• Wikidata: Q72459032
• ChEMBL ID: CHEMBL1688968
• Mol file: 2036-13-7.mol

Synonyms:6-cyanopurine

Chemical Property of 6-Cyanopurine

Chemical Property:

• Vapor Pressure: 0.00496mmHg at 25°C
• Melting Point: 186-189 °C(lit.)
• Refractive Index: 1.852
• Boiling Point: 529.5 °C at 760 mmHg
• Flash Point: 161.9 °C
• PSA: 78.25000
• Density: 1.56 g/cm³
• LogP: 0.22458
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 145.03884512
• Heavy Atom Count: 11
• Complexity: 194

Purity/Quality:

97% ^*data from raw suppliers

6-Cyanopurine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC2=NC=NC(=C2N1)C#N
• General Description: 6-Cyanopurine is a purine derivative that serves as a key intermediate in the synthesis of pyrimido[5,4-d]pyrimidine N-oxides, which are structurally related to purines and exhibit potential biological activity. In the described method, 6-cyanopurine reacts with benzylhydroxylamine to form an intermediate, which, depending on the solubility of its hydrochloride, can be further transformed into rearranged products or N-oxides. This highlights its utility in mild and selective synthetic routes for heterocyclic compounds relevant to pharmaceutical development.

Technology Process of 6-Cyanopurine

There total 7 articles about 6-Cyanopurine 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: 95.0%

6-cyano-9-(tetrahydropyran-2-yl)purine (165546-07-6) → 6-cyanopurine (2036-13-7)

Guidance literature:

With Dowex 50X₈ (H⁺); water; In methanol; for 1h; Heating;

DOI:10.1135/cccc19951386

Reference yield: 48.0%

C5H3N5(CHN(CH3)2) → 6-cyanopurine (2036-13-7)

Guidance literature:

In ethanol; at 20 ℃; for 1.5h;

DOI:10.1002/ejoc.200700416

Reference yield:

6-iodopurine (2545-26-8) → 6-cyanopurine (2036-13-7)

Guidance literature:

In methanol;

upstream raw materials:

6-iodo-7H-purine

6-cyano-9-(tetrahydropyran-2-yl)purine

6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

6-iodopurine

Downstream raw materials:

C-(7(9)H-purin-6-yl)-methylamine

7H-purine-6-carboxylic acid

6-Carbamidopurin

6-Thiocarboxamidopurin

Refernces

A mild approach to the synthesis of 4-amino-8-(arylamino)pyrimido[5,4-d] pyrimidine 3-oxides

10.1002/ejoc.200900216

The research presents a novel and efficient method for synthesizing pyrimido[5,4-d]pyrimidine N-oxides, which are of significant interest in drug development due to their structural similarity to purines and their potential biological activities. The study explores the reaction of benzylhydroxylamine with 6-cyanopurines to form 7-benzyloxy-8-imino-7,8-dihydropyrimido[5,4-d]pyrimidines, which upon treatment with hydrochloric acid, yield the desired N-oxides. The study concludes that the solubility of the hydrochloride of the intermediate pyrimido-pyrimidines in the reaction solvent plays a crucial role in determining the final product, with soluble hydrochlorides leading to the rearranged product and insoluble ones yielding the N-oxides. This work provides a mild and selective approach to synthesizing these heterocyclic compounds, which could have implications for the development of new pharmaceutical agents.