6-Chloro Acyclovir Acetate

Base Information

• Chemical Name: 6-Chloro Acyclovir Acetate
• CAS No.: 81777-48-2
• Molecular Formula: C10H12ClN5O3
• Molecular Weight: 285.69
• Mol file: 81777-48-2.mol

Synonyms:9-[(2-acetoxyethoxy)methyl]-2-amino-6-chloro-9H-purine;9-<(2-acetoxyethoxy)methyl>-2-amino-6-chloropurine;2-[(2-amino-6-chloro-9h-purin-9-yl)methoxy]ethyl acetate;2-amino-6-chloro-9-(2-acetoxyethoxymethyl)purine;9-[(2-Acetoxyethoxy)methyl]-2-amino-6-chloropurin;6-Chloro Acyclovir Acetate;

Chemical Property of 6-Chloro Acyclovir Acetate

Chemical Property:

• Vapor Pressure: 1.28E-11mmHg at 25°C
• Melting Point: 123-125oC
• Boiling Point: 537.3oC at 760 mmHg
• Flash Point: 278.8oC
• PSA: 105.88000
• Density: 1.61g/cm3
• LogP: 0.52920
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99.90% ^*data from raw suppliers

6-Chloro Acyclovir Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 6-Chloro Acyclovir Acetate (cas# 81777-48-2) is a compound useful in organic synthesis.

Technology Process of 6-Chloro Acyclovir Acetate

There total 4 articles about 6-Chloro Acyclovir Acetate 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: 66.0%

9-[(acetoxyethoxy)methyl]guanine (102728-64-3) → 9-<(2-acetoxyethoxy)methyl>-2-amino-6-chloro-9H-purine (81777-48-2)

Guidance literature:

With 2,4,6-trimethyl-pyridine; tetraethylammonium chloride; trichlorophosphate; In acetonitrile; for 0.166667h; Heating;

DOI:10.1055/s-1990-26904

Reference yield: 65.0%

1,3-DIOXOLANE (646-06-0) + acetic anhydride (108-24-7) + 2-Amino-6-chloropurin (10310-21-1) → 9-<(2-acetoxyethoxy)methyl>-2-amino-6-chloro-9H-purine (81777-48-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 0.25h; regioselective reaction;

DOI:10.3390/molecules25184307

Reference yield:

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one (75128-73-3) → 9-<(2-acetoxyethoxy)methyl>-2-amino-6-chloro-9H-purine (81777-48-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / triethylamine / ethanol / 10 h / Heating

2: 66 percent / Et₄NCl, 2,4,6-trimethylpyridine, POCl₃ / acetonitrile / 0.17 h / Heating

With 2,4,6-trimethyl-pyridine; tetraethylammonium chloride; triethylamine; trichlorophosphate; In ethanol; acetonitrile;

DOI:10.1055/s-1990-26904

upstream raw materials:

9-[(acetoxyethoxy)methyl]guanine

2-acetoxyethoxymethyl bromide

2-Amino-6-chloropurin

1,1,1,3,3,3-hexamethyl-disilazane

Downstream raw materials:

deoxyacyclovir

acycloguanosine

2-amino-6-chloro-9-<(2-hydroxyethoxy)methyl>-9H-purine

Refernces

• 1、 Stimac,Kobe. "A new synthesis of acyclovir prodrugs. N2-acetylacyclovir and 6-deoxyacyclovir". . p. 461 - 464. Retrieved 2007/10/02.
• 2、 Robins,Hatfield. "Nucleic acid related compounds. 37. Convenient and high-yield syntheses of N-[(2-hydroxyethoxy)methyl] heterocycles as 'acyclic nucleoside' analogues". . p. 547 - 553. Retrieved 2007/10/02.