6-HYDROXY-2-METHYLAMINOPURINE

Base Information

• Chemical Name: 6-HYDROXY-2-METHYLAMINOPURINE
• CAS No.: 10030-78-1
• Molecular Formula: C6H7 N5 O
• Molecular Weight: 165.15
• Hs Code.: 2933990090
• Mol file: 10030-78-1.mol

Synonyms:6H-Purin-6-one,1,7-dihydro-2-(methylamino)- (9CI); Guanine, N-methyl- (6CI,7CI,8CI);2-(Methylamino)-6-hydroxypurine; 2-Methylamino-6-oxopurine;6-Hydroxy-2-(methylamino)purine; N2-Methylguanine; NSC 90400

Chemical Property of 6-HYDROXY-2-METHYLAMINOPURINE

Chemical Property:

• Vapor Pressure: 0.00389mmHg at 25°C
• Boiling Point: 488.2°Cat760mmHg
• Flash Point: 249.1°C
• PSA: 86.72000
• Density: 1.79g/cm³
• LogP: 0.17320
• Storage Temp.: 4°C, Inert atmosphere

Purity/Quality:

97% ^*data from raw suppliers

2-(Methylamino)-6,7-dihydro-3H-purin-6-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 6-HYDROXY-2-METHYLAMINOPURINE (also known as N2-Methylguanine) is an N2-substituted guanine derivative synthesized through a method involving the reaction of 2-chloro-7-benzylhypoxanthine with methylamine, followed by debenzylation via palladium-catalyzed hydrogenation. 6-HYDROXY-2-METHYLAMINOPURINE is part of a broader class of N2-alkylguanines, which are of interest for their potential biological activity. The synthetic approach highlights the accessibility of starting materials and efficient yields, positioning N2-Methylguanine as a viable candidate for further biochemical or pharmaceutical applications.

Technology Process of 6-HYDROXY-2-METHYLAMINOPURINE

There total 8 articles about 6-HYDROXY-2-METHYLAMINOPURINE 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: 85.0%

tert-butyl 2-[(tert-butoxycarbonyl)(methyl)amino]-6-chloro-9H-purine-9-carboxylate → 2-methyamino-6-hydroxypurine (10030-78-1)

Guidance literature:

With formic acid; water; at 75 ℃; for 2h;

DOI:10.1134/S1070428019060198

Reference yield: 73.0%

7-Benzyl-2-methylamino-1,7-dihydro-purin-6-one → 1,7-dihydro-2-(methylamino)-6H-purin-6-one (10030-78-1)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In water; at 85 - 90 ℃;

DOI:10.1007/bf01169255

Reference yield:

2-methylsulfanyl-1,7(9)-dihydro-purin-6-one (5446-89-9) + methylamine (74-89-5) → 1,7-dihydro-2-(methylamino)-6H-purin-6-one (10030-78-1)

Guidance literature:

With water; at 140 ℃;

DOI:10.1021/ja01582a060

upstream raw materials:

2-methylsulfanyl-1,7⁽⁹⁾-dihydro-purin-6-one

methylamine

7-benzyl-2-chloro-1,7-dihydro-purin-6-one

2-thioxanthine

Downstream raw materials:

2-methylamino-1,7-dihydro-purine-6-thione

N₂-Methylguanosine

Refernces

Synthesis of N²-alkyl(aryl, dialkyl, cycloalkyl)guanines

10.1007/bf01169255

The study presents a novel method for synthesizing N2-substituted guanines, which are important in the creation of biologically active materials. The researchers used 2-chloro-7-benzylhypoxanthine as the starting material and reacted it with various amines, including primary and secondary aliphatic, aromatic, and alicyclic amines, to produce N2-substituted 7-benzylguanines. These intermediates were then subjected to palladium-catalyzed hydrogenation to remove the benzyl group, yielding the final N2-substituted guanines. The synthesized compounds include N2-methylguanine, N2-phenylguanine, and N2-dimethylguanine, among others. The method is advantageous due to the availability of starting materials and the relatively high yields of the final products, making it a potentially useful approach for the preparation of these biologically significant compounds.