9-(4-Acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine

Base Information

• Chemical Name: 9-(4-Acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine
• CAS No.: 97845-60-8
• Molecular Formula: C14H18ClN5O4
• Molecular Weight: 355.781
• European Community (EC) Number: 619-293-7
• UNII: V9DM57H0B7
• DSSTox Substance ID: DTXSID60436245
• Nikkaji Number: J1.484.494E
• Wikidata: Q72434274
• Mol file: 97845-60-8.mol

Synonyms:97845-60-8;2-(2-(2-Amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyl diacetate;9-(4-acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine;9-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine;6-Chloro famciclovir;C14H18ClN5O4;V9DM57H0B7;[2-(acetyloxymethyl)-4-(2-amino-6-chloropurin-9-yl)butyl] acetate;2-(2-(2-Amino-6-chloro-9H-purin-9-yl)-ethyl)propane-1,3-diyl diacetate;EC 619-293-7;9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloropurine;9-(4-Acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloro purine;[2-(acetoxymethyl)-4-(2-amino-6-chloro-purin-9-yl)butyl] acetate;(2-(ACETYLOXYMETHYL)-4-(2-AMINO-6-CHLOROPURIN-9-YL)BUTYL) ACETATE;9-(4-ACETOXY-3-(ACETOXYMETHYL)BUTYL)-2-AMINO-6-CHLOROPURINE;1,3-Propanediol, 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-, 1,3-diacetate;1,3-Propanediol, 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-, diacetate (ester) (9CI);6-Chloro Famciclovir;6-Chlorofamciclovir;UNII-V9DM57H0B7;The intermediate of Famciclovir;SCHEMBL3155583;DTXSID60436245;BCP11984;MFCD08458206;2-(2-(2-Amino-6-chloro-9H-purin-9-yl)ethyl)propane-1,3-diyldiacetate;AKOS015892535;AC-9090;1,3-Propanediol,2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]diacetate(ester)(9Cl;BS-42437;6-CHLORO FAMCICLOVIR [USP IMPURITY];CS-0155003;FT-0642347;FT-0661061;Penciclovir Impurity E;A845755;9-(4-acetoxy-3-acetoxymethyl butyl)-2-amino-6-chloropurine;9-(4-acetoxy-3-acetoxymethylbut-l-yl)-2-amino-6-chloropurine;2-AMINO-6-CHLORO-9-(4-ACETOXY-3-ACETOXYMETHYLBUTYL)PURINE;6-Chloro-9-[3-(acetoxymethyl)-4-acetoxybutyl]-9H-purine-2-amine;9-(4-acetoxy-3-acetoxymethyl-but-1-yl)-2-amino-6-chloropurine;2-[(acetyloxy)methyl]-4-(2-amino-6-chloro-9H-purin-9-yl)butyl acetate;Acetic acid 2-acetoxymethyl-4-(2-amino-6-chloro-purin-9-yl)-butyl ester;1,1'-(2-(2-(2-AMINO-6-CHLORO-9H-PURIN-9-YL)ETHYL)-1,3-PROPANEDIYL) DIACETATE;1,3-PROPANEDIOL, 2-(2-(2-AMINO-6-CHLORO-9H-PURIN-9-YL)ETHYL)-, 1,3-DIACETATE;2-[(Acetyloxy)methyl]-4-(2-amino-6-chloro-9H-purin-9-yl)butyl acetate (non-preferred name);2-[2-(2-Amino-6-chloro-9H-purin-9-yl)ethyl]-1,3-propanediol 1,3-Diacetate;Esterified Compound Intermediate

Chemical Property of 9-(4-Acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 132-134 °C(Solv: isopropanol (67-63-0))
• Refractive Index: 1.64
• Boiling Point: 574.979 °C at 760 mmHg
• PKA: 2.23±0.10(Predicted)
• Flash Point: 301.536 °C
• PSA: 122.22000
• Density: 1.496 g/cm³
• LogP: 1.77560
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 355.1047318
• Heavy Atom Count: 24
• Complexity: 437

Purity/Quality:

99% ^*data from raw suppliers

9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloropurine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(CCN1C=NC2=C1N=C(N=C2Cl)N)COC(=O)C
• Uses: 9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-amino-6-chloropurine is an impurity of Famciclovir (F101125), an antiviral agent and a prodrug of Penciclovir (P221500).

Technology Process of 9-(4-Acetoxy-3-acetoxymethylbut-1-yl)-2-amino-6-chloropurine

There total 43 articles about 9-(4-Acetoxy-3-acetoxymethylbut-1-yl)-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: 80.8%

acetic anhydride (108-24-7) + 2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (172529-94-1) → 9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine (97845-60-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

Reference yield: 80.0%

2-acetoxymethyl-4-bromobut-1-yl-acetate + 2-Amino-6-chloropurin (10310-21-1) → 9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine (97845-60-8) + 7-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine (97845-61-9)

Guidance literature:

With potassium carbonate; In N-methyl-acetamide; chloroform;

Reference yield: 70.0%

2-[(acetyloxy)methyl]-4-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)butyl acetate (97845-72-2) → 9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine (97845-60-8)

Guidance literature:

With tetraethylammonium chloride; N,N-dimethyl-aniline; trichlorophosphate; In acetonitrile; at 70 ℃; for 1h;

DOI:10.1016/j.tet.2006.03.080

upstream raw materials:

4-acetoxy-3-(acetoxymethyl)-1-iodobutane

2-Amino-6-chloropurin

acetic anhydride

2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine

Downstream raw materials:

9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine

Penciclovir

2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine

6-deoxypenciclovir

Refernces

• 1、 -. "Method for preparing 2-amino-6-chloro-9-(4-acetoxy-3-acetoxymethylbutyl)purine". Paragraph 0019-0020; 0038. . Retrieved 2018/08/03.
• 2、 Derudas, Marco,Vanpouille, Christophe,Carta, Davide,Zicari, Sonia,Andrei, Graciela,Snoeck, Robert,Brancale, Andrea,Margolis, Leonid,Balzarini, Jan,McGuigan, Christopher. "Virtual Screening of Acyclovir Derivatives as Potential Antiviral Agents: Design, Synthesis, and Biological Evaluation of New Acyclic Nucleoside ProTides". supporting information. p. 7876 - 7896. Retrieved 2017/10/06.