(6-Amino-9H-purin-9-yl)acetic acid

Base Information

• Chemical Name: (6-Amino-9H-purin-9-yl)acetic acid
• CAS No.: 20128-29-4
• Molecular Formula: C7H7N5O2
• Molecular Weight: 193.165
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00470022
• Nikkaji Number: J531.117I
• Wikidata: Q82297982
• Mol file: 20128-29-4.mol

Synonyms:20128-29-4;(6-Amino-9H-purin-9-yl)acetic acid;6-Amino-9H-purine-9-acetic Acid;2-(6-Amino-9H-purin-9-yl)acetic acid;2-(6-aminopurin-9-yl)acetic Acid;9H-Purine-9-acetic acid, 6-amino-;Adenin-9-ylacetic Acid;SCHEMBL1673251;DTXSID00470022;MFCD16074138;AKOS010941619;2-(6-Amino-9H-purin-9-yl)aceticacid;CS-0449271;FT-0662042;EN300-145681;A926098;J-013036

Chemical Property of (6-Amino-9H-purin-9-yl)acetic acid

Chemical Property:

• PSA: 106.92000
• LogP: 0.07430
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 193.05997448
• Heavy Atom Count: 14
• Complexity: 236

Purity/Quality:

99.90% ^*data from raw suppliers

6-Amino-9H-purine-9-acetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)CC(=O)O)N
• Uses: A metabolite of Adefovir (A247500) and Remofovir.

Technology Process of (6-Amino-9H-purin-9-yl)acetic acid

There total 7 articles about (6-Amino-9H-purin-9-yl)acetic acid 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%

ethyl 2-(9H-adenin-9-yl)acetate (25477-96-7) → 2-(6-amino-9H-purin-9-yl)acetic acid (20128-29-4)

Guidance literature:

With sodium hydroxide; In methanol; at 0 ℃; for 0.5h;

DOI:10.1021/jo971162p

Reference yield: 86.8%

2-(N9-adeninyl)acetic acid methyl ester (23124-10-9) → 2-(6-amino-9H-purin-9-yl)acetic acid (20128-29-4)

Guidance literature:

With water; sodium hydroxide; In methanol; for 12h;

DOI:10.1016/j.ica.2018.09.041

Reference yield:

7H-purin-6-ylamine (73-24-5,71660-29-2,71660-30-5) → 2-(6-amino-9H-purin-9-yl)acetic acid (20128-29-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

1.2: 24 h / 0 °C / Inert atmosphere

2.1: water; sodium hydroxide / methanol / 12 h

With water; potassium carbonate; sodium hydroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.ica.2018.09.041

upstream raw materials:

ethyl 2-(9H-adenin-9-yl)acetate

tert-butyl 2-(6-amino-9H-purin-9-yl)acetate

adenine

2-(N₉-adeninyl)acetic acid methyl ester

Refernces

• 1、 Mohapatra, Balaram,Pratibha,Saravanan, R. Kamal,Verma, Sandeep. "2,6-Diaminopurine-zinc complex for primordial carbon dioxide fixation". . p. 167 - 173. Retrieved 2019.
• 2、 Mishra, Ashutosh Kumar,Kumar, Jitendra,Khanna, Shruti,Verma, Sandeep. "Crystallographic signatures of cobalt coordination with modified adenine nucleobase containing carboxyl group pendants". . p. 1623 - 1630. Retrieved 2011.
• 3、 Zhu, Mei,Dong, Biao,Zhang, Guo-Ning,Wang, Ju-Xian,Cen, Shan,Wang, Yu-Cheng. "Synthesis and biological evaluation of new HIV-1 protease inhibitors with purine bases as P2-ligands". supporting information. p. 1541 - 1545. Retrieved 2019/04/25.