2-Amino-6-chloropurine

Base Information

• Chemical Name: 2-Amino-6-chloropurine
• CAS No.: 10310-21-1
• Molecular Formula: C5H4ClN5
• Molecular Weight: 169.573
• Hs Code.: DERIVATION
• European Community (EC) Number: 233-686-7
• NSC Number: 29570
• UNII: 83V03P835E
• DSSTox Substance ID: DTXSID9074432
• Nikkaji Number: J236.697E
• Wikidata: Q27139921
• Pharos Ligand ID: URVXHJKJH7CW
• Metabolomics Workbench ID: 65954
• ChEMBL ID: CHEMBL226396
• Mol file: 10310-21-1.mol

Synonyms:2-amino-6-chloropurine

Chemical Property of 2-Amino-6-chloropurine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.75E-15mmHg at 25°C
• Melting Point: 300 °C
• Refractive Index: 1.826
• Boiling Point: 623.9 °C at 760 mmHg
• PKA: 6.65±0.20(Predicted)
• Flash Point: 331.1 °C
• PSA: 80.48000
• Density: 1.77 g/cm³
• LogP: 1.16970
• Storage Temp.: Keep Cold
• Solubility.: Solubility in 1mol/L NaOH; very faint turbidity.
• Water Solubility.: 1.7 g/L (20 ºC)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 169.0155228
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-6-chloropurine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N1)C(=NC(=N2)N)Cl
• Description: 6-Chloroguanine, also be known as 2-Amino-6-chloropurine may be used in the enzymatic synthesis of 2′-deoxyguanosine, 9-alkyl purines (R)and (S)-N(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. It is also useful during the synthesis of guanine. 2-Amino-6-chloropurine is a precursor in the synthesis of nucleoside analogs with antiviral activity against Epstein-Barr virus (EBV) and human herpes virus 6 (HHV-6).
• Uses: 2-Amino-6-chloropurine may be used:in the enzymatic synthesis of 2′-deoxyguanosinein the synthesis of 9-alkyl purinesin the synthesis of (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases 2-Amino-6-chloropurine finds its uses in the enzymatic synthesis of 2?-deoxyguanosine, 9-alkyl purines and (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases.

Technology Process of 2-Amino-6-chloropurine

There total 23 articles about 2-Amino-6-chloropurine 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: 96.2%

N2-acetylguanine (19962-37-9) → 2-Amino-6-chloropurin (10310-21-1)

Guidance literature:

N²-acetylguanine; With N-methylcyclohexylamine; thionyl chloride; 1,1,1,3,3,3-hexachloro-propan-2-one; at 85 ℃; for 24h;

With sodium hydroxide; In water; at 25 ℃; for 6h; Reagent/catalyst;

Reference yield: 96.2%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + C4H4ClN5O → 2-Amino-6-chloropurin (10310-21-1)

Guidance literature:

formaldehyd; C₄H₄ClN₅O; With sodium pyrosulfate; In water; at 70 - 115 ℃; for 3h;

With toluene-4-sulfonic acid; In toluene; at 105 - 110 ℃; for 18h;

Reference yield: 94.0%

Guanine (8039-79-0) → 2-amino-6-chloropurine (10310-21-1)

Guidance literature:

With thionyl chloride; dihydrogen peroxide; at 40 ℃; for 3h; Temperature;

upstream raw materials:

thioguanin

2,9-diacetylguanine

2-amino-1,9-dihydro-6H-purin-6-one

formic acid

Downstream raw materials:

thioguanin

2-amino-6-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine

2-amino-6-chloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl)-9H-purine

(3'R,5'R)-1-<5'-<(benzyloxy)methyl>tetrahydro-3'-thienyl>-6-chloro-9H-purin-6-amine

Refernces

Synthesis and conformational study of 3-hydroxy-4-(hydroxymethyl)-1-cyclohexanyl purines and pyrimidines

10.1021/jo962204x

This research study on the synthesis and conformational analysis of cyclohexane nucleosides, specifically focusing on 3-hydroxy-4-(hydroxymethyl)-1-cyclohexanyl purines and pyrimidines. The purpose of the study was to understand the correlation between the antiviral activity of these compounds and their conformational structure. The researchers synthesized the nucleosides using various nucleobases and ethyl 1,3-cyclohexadiene-1-carboxylate through a conjugated addition reaction and hydroboration of the cyclohexenyl precursor. Key chemicals used in the synthesis process included adenine, 2-amino-6-chloropurine, thymine, uracil, cytosine, and various protecting groups like monomethoxytrityl and trityl groups, as well as reagents such as DBU, TFA, and BH3-THF complex. The lack of antiviral activity observed in the synthesized compounds was linked to their conformation, which was deduced from NMR and X-ray analysis. The study concluded that the replacement of the ring oxygen with a methylene group in carbocyclic nucleosides led to a change in the preferred conformation of the nucleoside base from axial to equatorial, which might explain the loss of antiviral activity compared to anhydrohexitol nucleosides.