97845-60-8

Basic information

• Product Name: 9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine
• Synonyms: 9-(4-ACETOXY-3-ACETOXYMETHYLBUT-1-YL)-2-AMINO-6-CHLOROPURINE;9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chl;9-(4-ACETOXY-3-ACETOXYMETHYLBUT-1-YL)-2-AMINO-6-CHLOROPUINE;9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine;1,3-Propanediol,2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]diacetate(ester)(9Cl;9-(4-Acetoxy-3-aceto;2-(2-(2-AMino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate;9-(4-ACETOXY-3)-ACETOXYMETHYLBURYL-2-AMINO-6-CHLOROPURINE
• CAS NO: 97845-60-8
• Molecular Formula: C₁₄H₁₈ClN₅O₄
• Molecular Weight: 355.78
• EINECS: 1308068-626-2
• Product Categories: API intermediates
• Mol File: 97845-60-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 132-134 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 574.979 °C at 760 mmHg
• Flash Point: 301.536 °C
• Appearance: /
• Density: 1.496 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.23±0.10(Predicted)
• CAS DataBase Reference: 9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine(97845-60-8)
• EPA Substance Registry System: 9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine(97845-60-8)

Safety Data

• Hazardous Substances Data: 97845-60-8(Hazardous Substances Data)

Usage

Description

9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine is a chemical compound that serves as an impurity in Famciclovir (F101125), an antiviral agent and a prodrug of Penciclovir (P221500).

Uses

Used in Pharmaceutical Industry:
9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine is used as an impurity in the production of Famciclovir, an antiviral agent. Famciclovir is a prodrug of Penciclovir, which is used to treat various viral infections, including herpes simplex and varicella-zoster virus infections. The presence of this impurity may affect the efficacy and safety of the antiviral treatment.

InChI:InChI=1/C14H18ClN5O4/c1-8(21)23-5-10(6-24-9(2)22)3-4-20-7-17-11-12(15)18-14(16)19-13(11)20/h7,10H,3-6H2,1-2H3,(H2,16,18,19)

Upstream product

• 127047-77-2 4-acetoxy-3-(acetoxymethyl)-1-iodobutane 
• 10310-21-1 2-Amino-6-chloropurin 
• 118-00-3 G 
• 128139-38-8 Acetic acid 2-acetoxymethyl-4-methanesulfonyloxy-butyl ester 
• 122497-17-0 2-[2-(2-Amino-6-chloro-purin-9-yl)-ethyl]-2-ethoxycarbonyl-malonic acid diethyl ester 
• 71170-82-6 triethyl 3-bromopropane-1,1,1-tricarboxylate 
• 126589-88-6 1,3-diacetoxy-2-(2-hydroxyethyl)propane 
• 10310-21-1 2-amino-6-chloropurine 
• 105-70-4 2-hydroxypropane-1,3-diyl diacetate 
• 214201-64-6 9-(2-bromoethyl)-6-chloro-9H-purin-2-amine 
• 126589-82-0 2-Acetoxymethyl-4-bromobut-1-yl acetate 
• 131266-10-9 2-acetoxymethyl-4-benzyloxybutyl acetate 
• 77661-80-4 2-(2-(benzyloxy)ethyl)propane-1,3-diol 
• 172529-93-0 2-amino-6-chloro-9-(3,3-dimethoxycarbonyl-1-propyl)purine 

Downstream Products

• 104227-86-3 6-deoxypenciclovir 
• 120687-07-2 (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine 
• 120687-10-7 (R,S)-2-amino-9-<4-(benzyloxy)-3-(hydroxymethyl)but-1-yl>purine 
• 115932-75-7 9-<4-hydroxy-3-(hydroxymethyl)but-1-yl>-2-<(monomethoxytrityl)amino>purine 
• 120711-22-0 (R,S)-9-<3-(hydroxymethyl)-4-<(monomethoxytrityl)oxy>but-1-yl>-2-<(monomethoxytrityl)amino>purine 
• 104227-87-4 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine 
• 172529-94-1 2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine 
• 39809-25-1 Penciclovir 

Relevant articles and documents

Preparation method of penciclovir

The invention discloses a preparation method of penciclovir. An existing synthetic route mainly has the following defects that the N-7 site by-products need to be removed through column chromatography, a large amount of three wastes are generated, and the yield of N-9 site products is not high. According to the technical scheme adopted by the invention, the preparation method comprises the following steps: carrying out alkylation on 2-amino-6-chloropurine and triethyl bromopropane under an alkaline condition to introduce an N-9 site side chain, carrying out decarboxylation and transesterification in a methanol solution of sodium methoxide to generate the 2-amino-6-chloro-9-(3,3-dimethoxycarbonyl-1-propyl)purine; then reducing the 2-amino-6-chloro-9-(3,3-dimethoxycarbonyl-1-propyl)purine togenerate 2-amino-6-chloro-9-(3-hydroxymethyl-4-hydroxy-1-butyl)purine with sodium borohydride; and finally, directly hydrolyzing under acidic conditions to obtain penciclovir. According to the method, the target product is obtained by directly hydrolyzing the reduction product, ester group protection and deprotection are not needed, and the method has the advantages of few reaction steps, good product quality, simplicity and convenience in operation, suitability for industrial production and the like.

Method for preparing 2-amino-6-chloro-9-(4-acetoxy-3-acetoxymethylbutyl)purine

The invention relates to a method for preparing 2-amino-6-chloro-9-(4-acetoxy-3-acetoxymethylbutyl)purine. The method comprises the following steps: reacting 1,3-dichloro-2-propanol with acetic acid to obtain 1,3-diacetoxy-2-propanol, brominating the 1,3-diacetoxy-2-propanol to obtain 1,3-diacetoxy-2-bromopropane, and reacting the 1,3-diacetoxy-2-bromopropane with zinc powder to obtain 1,3-diacetoxy-2-propylzinc bromide, and then performing a Negishi Coupling reaction on the 1,3-diacetoxy-2-propylzinc bromide and chloro-9-bromoethylpurine to obtain 2-amino-6-chloro-9-(4-acetoxy-3-acetoxymethylbutyl)purine. The obtained 2-amino-6-chloro-9-(4-acetoxy-3-acetoxymethylbutyl)purine has an HPLC purity of 99.5% or more, and can be used for producing famciclovir and penciclovir.

A process for the manufacture of famciclovir using phase-transfer catalysts

The invention relates to a process for the preparation of Famciclovir, which comprises the preparation of a compound of formula (II) wherein X is a halogen atom by reaction of a compound of formula (III) with a compound of formula (VII) wherein L is a leaving group, in the presence of a catalytic amount of a quaternary ammonium salt, followed by hydrogenation of compound (II) to Famciclovir.