6-Methyladenine

Base Information

• Chemical Name: 6-Methyladenine
• CAS No.: 443-72-1
• Molecular Formula: C6H7N5
• Molecular Weight: 149.155
• Hs Code.: 2933990090
• European Community (EC) Number: 207-137-7
• NSC Number: 11580
• UNII: W7IBY2BGAX
• DSSTox Substance ID: DTXSID1020857
• Nikkaji Number: J128.125I
• Wikidata: Q15632800
• Metabolomics Workbench ID: 38021
• ChEMBL ID: CHEMBL1738843
• Mol file: 443-72-1.mol

Synonyms:6-methyladenine;6-methylaminopurine;m6A;N(6)-methyladenine

Chemical Property of 6-Methyladenine

Chemical Property:

• Vapor Pressure: 0.0153mmHg at 25°C
• Melting Point: ≥300 °C
• Refractive Index: 1.792
• Boiling Point: 492.9 °C at 760 mmHg
• PKA: 9.61±0.20(Predicted)
• Flash Point: 251.9 °C
• PSA: 66.49000
• Density: 1.476 g/cm³
• LogP: 0.46760
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 149.07014524
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

97% ^*data from raw suppliers

N6-Methyladenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=NC=NC2=C1NC=N2
• General Description: 6-(Methylamino)purine (also known as 6-MAP, N6-methyladenine, or 6-methyladenine) is a purine derivative that serves as a key intermediate in the synthesis of biologically active compounds, such as the anticonvulsant agent 9-(2-fluorobenzyl)-6-methylamino-9H-purine. It is utilized in various synthetic routes, demonstrating its versatility as a precursor in medicinal chemistry. The compound's structure, featuring a methylamino group at the 6-position of the purine ring, contributes to its reactivity in alkylation and amination reactions, making it valuable for the development of therapeutic agents.

Technology Process of 6-Methyladenine

There total 28 articles about 6-Methyladenine 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: 97.0%

methylamine (74-89-5) + 6-chloropurine hydrochloride → N-methyladenine (443-72-1)

Guidance literature:

In tetrahydrofuran; ethanol; at 120 ℃; for 2h;

DOI:10.1016/S0223-5234(02)01446-0

Reference yield: 90.0%

6-chloro-7H-purine (87-42-3,111055-92-6) + methylamine (74-89-5) → N-methyladenine (443-72-1)

Guidance literature:

In methanol; ethanol; at 120 ℃; for 4h; Sealed tube;

Reference yield: 75.0%

Benzotriazol-1-ylmethyl-(9H-purin-6-yl)-amine (111098-24-9) → N-methyladenine (443-72-1)

Guidance literature:

With sodium tetrahydroborate; In 1,4-dioxane; for 20h; Heating;

upstream raw materials:

1-methyl-1,7⁽⁹⁾-dihydro-purine-6-thione

methylamine

6-(methylthio)-1H-purine

6H-purine-6-thione

Downstream raw materials:

methyl-nitroso-(7(9)H-purin-6-yl)-amine

N⁶-methyladenosine

9-(2-chloro-6-fluorobenzyl)-6-methylaminopurine

methyl-(9-benzyl-9H-purin-6-yl)amine

Refernces

Synthesis of 9-(2-fluorobenzyl)-6-methylamino-9H-purine

10.1002/jhet.5570230445

The research details the synthesis of 9-(2-fluorobenzyl)-6-methylamino-9H-purine (1), a novel anticonvulsant agent with potent activity against maximal electroshock-induced seizures in rats and mice. The study explores nine different synthetic routes to compound 1, utilizing various precursors such as 6-chloro-9-(2-fluorobenzyl)-9H-purine (4), 6-methylaminopurine (5), and 9-(2-fluorobenzyl)-1-methyladeninium iodide (8). Key chemicals involved in the synthesis process include 5-amino-4,6-dichloropyrimidine, 2-fluorobenzylamine, ethanol, triethylamine, ethanesulfonic acid, and triethylorthoformate, among others. The preferred route was found to be the condensation of 5-amino-4,6-dichloropyrimidine with 2-fluorobenzylamine, followed by a series of reactions including alkylation, amination, and rearrangement, ultimately yielding the desired compound 1. The conclusions of the research highlight the efficiency and adaptability of the chosen synthetic route for preparing compound 1 and its analogues from readily available starting materials.