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

Base Information

• Chemical Name: 9-(2-fluorobenzyl)-6-(methylamino)-9H-purine
• CAS No.: 101155-02-6
• Molecular Formula: C13H12 F N5
• Molecular Weight: 257.27
• UNII: DX8S5Q0N0S
• DSSTox Substance ID: DTXSID50143759
• Nikkaji Number: J399.560G
• Wikidata: Q83007753
• ChEMBL ID: CHEMBL7359
• Mol file: 101155-02-6.mol

Synonyms:9-(2-fluorobenzyl)-6-(methylamino)-9H-purine;9-(2-fluorobenzyl)-6-(methylamino)-9H-purine hydrochloride;BW A78U;BW-A 78U;BW-A-78U;BW-A78U

Chemical Property of 9-(2-fluorobenzyl)-6-(methylamino)-9H-purine

Chemical Property:

• Vapor Pressure: 2.69E-09mmHg at 25°C
• Boiling Point: 477.9°Cat760mmHg
• Flash Point: 242.8°C
• PSA: 55.63000
• Density: 1.36g/cm³
• LogP: 2.12840
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 257.10767357
• Heavy Atom Count: 19
• Complexity: 303

Purity/Quality:

98%min ^*data from raw suppliers

BW-A78U ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=C2C(=NC=N1)N(C=N2)CC3=CC=CC=C3F
• General Description: 9-(2-Fluorobenzyl)-6-(methylamino)-9H-purine (also known as BW-A 78U) is a novel anticonvulsant compound with demonstrated efficacy in suppressing maximal electroshock-induced seizures in rodent models. Its synthesis involves multiple optimized routes, with the preferred method starting from 5-amino-4,6-dichloropyrimidine and 2-fluorobenzylamine, followed by sequential alkylation, amination, and rearrangement steps. 9-(2-fluorobenzyl)-6-(methylamino)-9H-purine's structural modifications, including the 2-fluorobenzyl and methylamino groups, contribute to its potent pharmacological activity. The synthetic approach is adaptable for producing analogues, highlighting its potential for further anticonvulsant drug development.

Technology Process of 9-(2-fluorobenzyl)-6-(methylamino)-9H-purine

There total 21 articles about 9-(2-fluorobenzyl)-6-(methylamino)-9H-purine 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: 86.0%

9-(2-Fluorobenzyl)-6-(N-methylformamido)-9H-purine (101155-17-3) → BW-A 78U (101155-02-6)

Guidance literature:

With sodium hydroxide; In methanol; for 2.5h; Ambient temperature;

DOI:10.1002/jhet.5570230445

Reference yield: 83.0%

9-(2-Fluorobenzyl)-1-methyladeninium iodide → BW-A 78U (101155-02-6)

Guidance literature:

With sodium hydroxide; In methanol; for 60h; Ambient temperature;

DOI:10.1002/jhet.5570230445

Reference yield: 65.0%

6-(Dimethylaminomethyleneamino)-9-(2-fluorobenzyl)-9H-purine (101155-18-4) → BW-A 78U (101155-02-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; dimethyl sulfoxide; at 100 ℃; for 2h;

DOI:10.1002/jhet.5570230445

upstream raw materials:

9-(2-Fluorobenzyl)-6-formamido-9H-purine

8-Chloro-9-(2-fluorobenzyl)-6-methylamino-9H-purine

9-(2-Fluorobenzyl)-6-(N-methylformamido)-9H-purine

6-(Dimethylaminomethyleneamino)-9-(2-fluorobenzyl)-9H-purine

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.