2-Amino-6-chloro-9H-purine-9-acetic acid

Base Information

• Chemical Name: 2-Amino-6-chloro-9H-purine-9-acetic acid
• CAS No.: 149376-70-5
• Molecular Formula: C7H6 Cl N5 O2
• Molecular Weight: 227.61
• Hs Code.: 2933990090
• European Community (EC) Number: 623-716-0
• DSSTox Substance ID: DTXSID60400628
• Wikidata: Q82203634
• ChEMBL ID: CHEMBL2347308
• Mol file: 149376-70-5.mol

Synonyms:149376-70-5;2-Amino-6-chloro-9H-purine-9-acetic acid;2-(2-amino-6-chloro-9H-purin-9-yl)acetic acid;2-(2-amino-6-chloropurin-9-yl)acetic acid;2-Amino-6-Chloro-9-Carboxymethylpurine;9H-Purine-9-acetic acid, 2-amino-6-chloro-;SCHEMBL2153079;CHEMBL2347308;DTXSID60400628;LRZBBTTUKFVUMZ-UHFFFAOYSA-N;ZFA37670;AKOS024285766;3-O-ANISIDINEEROTONICACIDETHYLESTER;AS-65453;CS-0337144;2-(2-amino-6-chloro-9H-purin-9-yl)aceticacid;EN300-1688932;2-Amino-6-chloro-9H-purine-9-acetic acid, 97%;A910772;J-008586

Chemical Property of 2-Amino-6-chloro-9H-purine-9-acetic acid

Chemical Property:

• Vapor Pressure: 1.05E-15mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.853
• Boiling Point: 609.4°C at 760 mmHg
• PKA: 3.39±0.10(Predicted)
• Flash Point: 322.3°C
• PSA: 107.65000
• Density: 1.99g/cm³
• LogP: 0.07660
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 227.0210021
• Heavy Atom Count: 15
• Complexity: 266

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-(2-Amino-6-chloro-9H-purin-9-yl)aceticacid 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N1CC(=O)O)N=C(N=C2Cl)N
• Uses: 2-Amino-6-chloro-9H-purine-9-acetic acid may be used as starting material in the synthesis of:6-decyloxy substituted purine intermediates6-decylthio substituted purine intermediates6-decyloxy or 6-decylthio-9-phenylalanine/serine or alanine-substituted purine derivatives2,6-diaminopurine monomer

Technology Process of 2-Amino-6-chloro-9H-purine-9-acetic acid

There total 4 articles about 2-Amino-6-chloro-9H-purine-9-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: 100.0%

tert-butyl (6-chloro-2-aminopurin-9-yl)ethanoate (175695-32-6) → 2-amino-6-chloro-9-carboxymethylpurine (149376-70-5)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/0040-4039(96)00037-8

Reference yield: 71.0%

methyl 2-(2-amino-6-chloro-9H-purin-9-yl)acetate (172405-46-8) → 2-amino-6-chloro-9-carboxymethylpurine (149376-70-5)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 4h;

DOI:10.1016/S0040-4020(02)00527-6

Reference yield: 67.0%

bromoacetic acid (79-08-3) + 2-Amino-6-chloropurin (10310-21-1) → 2-amino-6-chloro-9-carboxymethylpurine (149376-70-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 20h; Inert atmosphere;

DOI:10.1039/c5ob02525g

upstream raw materials:

bromoacetic acid

2-Amino-6-chloropurin

tert-butyl (6-chloro-2-aminopurin-9-yl)ethanoate

methyl 2-(2-amino-6-chloro-9H-purin-9-yl)acetate

Downstream raw materials:

methyl N-((2-amino-6-(benzyloxy)purin-9-yl)acetyl)-N-(2-Boc-aminoethyl)glycinate

C₄₈H₅₈N₁₄O₁₂

C₄₇H₅₆N₁₄O₁₂

[[2-(2-Amino-6-benzyloxy-purin-9-yl)-acetyl]-(2-benzyloxycarbonylamino-ethyl)-amino]-acetic acid methyl ester

Refernces

• 1、 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.
• 2、 Stefan, Loic,Guedin, Aurore,Amrane, Samir,Smith, Nicole,Denat, Franck,Mergny, Jean-Louis,Monchaud, David. "DOTASQ as a prototype of nature-inspired G-quadruplex ligand". supporting information; experimental part. p. 4992 - 4994. Retrieved 2011/06/10.