7602-01-9

Basic information

• Product Name: 2-ACETAMIDO-6-CHLOROPURINE
• Synonyms: 2-ACETAMIDO-6-CHLOROPURINE;2-(Acetylamino)-6-chloropurine;N-(6-Chloro-9H-purin-2-yl)acetamide;N-(6-Chloro-7H-purin-2-yl)acetamide;N-(6-chloro-5H-purin-2-yl)acetamide
• CAS NO: 7602-01-9
• Molecular Formula: C₇H₆ClN₅O
• Molecular Weight: 211.60844
• Mol File: 7602-01-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: >300 °C
• Appearance: /
• Density: 1.80
• Refractive Index: 1.799
• PKA: 9.22±0.40(Predicted)
• CAS DataBase Reference: 2-ACETAMIDO-6-CHLOROPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETAMIDO-6-CHLOROPURINE(7602-01-9)
• EPA Substance Registry System: 2-ACETAMIDO-6-CHLOROPURINE(7602-01-9)

Safety Data

• Hazardous Substances Data: 7602-01-9(Hazardous Substances Data)

Usage

General Description

2-Acetamido-6-chloropurine is a chemical compound that belongs to the class of purine analogs. It is a synthetic derivative of purine and is commonly used as a starting material for the synthesis of various pharmaceutical compounds. 2-Acetamido-6-chloropurine exhibits biological activity as an antiviral and antitumor agent, making it a valuable compound in medicinal chemistry. Its molecular structure consists of a purine ring with a chlorine atom at the 6-position and an acetamido group at the 2-position, which gives it unique properties for use in the development of new drugs and therapeutic agents.

InChI:InChI=1/C7H6ClN5O/c1-3(14)11-7-12-5(8)4-6(13-7)10-2-9-4/h2,4H,1H3,(H,9,10,11,13,14)

Upstream product

• 108-24-7 acetic anhydride 
• 10310-21-1 2-Amino-6-chloropurin 
• 10310-21-1 2-amino-6-chloropurine 

Downstream Products

• 109303-94-8 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-2-acetamido-6-chloropurine 
• 140896-72-6 (E)-2-acetamido-9-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-4-(diisopropoxyphosphoryl)but-3-enyl>-6-chloropurine 
• 143056-35-3 N²-Acetyl-2-amino-6-chloro-9-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)purine 
• 143056-36-4 N²-Acetyl-2-amino-6-chloro-7-(2',3',4',6'-tetra-O-benzoyl-β-D-glucopyranosyl)purine 
• 214280-01-0 N-{9-[(3S,4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-thiophen-3-yl]-6-chloro-9H-purin-2-yl}-acetamide 
• 857896-63-0 N-[6-chloro-9-[(3aS,4S,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-2-yl]acetamide 
• 911110-85-5 N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]purine 
• 911110-88-8 N²-acetyl-9-[5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-trifluoroacetamido)ethyl-β-D-ribofuranosyl]guanine 
• 312745-86-1 N-{7-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-7H-purin-2-yl}acetamide 
• 312745-84-9 N-{7-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-β-D-ribofuranosyl}-7H-purin-2-yl}acetamide 
• 312745-80-5 N-{9-{5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxy-α-D-ribofuranosyl}-9H-purin-2-yl}acetamide 
• 103884-98-6 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine 

Relevant articles and documents

Synthesis of potentially prebiotic RNA precursors: Cytosine and guanine derivatives

The chemical synthesis of two potentially prebiotic monomers of RNA containing cytosine and guanine is reported.

Synthesis of the hepatitis B nucleoside analogue lagociclovir valactate

2′,3′-Dideoxy-3′-fluoro-5-O-[(S)-(+)-2-(l-valyloxy) -propionyl guanosine (lagociclovir valactate) is a prodrug of 3′-fluoro-2′,3′-dideoxyguanosine with high oral bioavailability in humans and potent activity against hepatitis B virus (HBV). A five-step synthesis of lagocyclovir valactate starting from 2-amino-6-chloropurine is described. The synthesis was performed at kilogram scale, and the target nucleoside prodrug was isolated as the hemisulphate salt with an overall yield of 23%. The major challenges were N-glycosylation of a 2-deoxyfluorosugar, which required separation of α- and β-anomers, and deprotection of the penultimate intermediate by hydrogenation.

Process for preparing 2-acetylamino-6-chloropurine

[OBJECT] To provide an intended product of high quality at low production costs in a yield higher than in ordinary processes by using an inexpensive catalyst or a catalyst which can be readily recovered. [ARRANGEMENT] A process for preparing 2-acetylamino-6-chloropurine comprises suspending 2,9-diacetylguanine or 2-acetylguanine in a polar inert solvent, reacting with phosphorus oxychloride in the presence of a water-insoluble tertiary amine and either ammonium chloride or a hydrochloride of the tertiary amine, and hydrolyzing the resultant reaction product to obtain 2-acetylamino-6-chloropurine.