9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine Chemical Properties

Melting point:

132-134 °C(Solv: isopropanol (67-63-0))

Boiling point:

575.0±60.0 °C(Predicted)

Density 

1.49±0.1 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

2.23±0.10(Predicted)

color 

Off-White to Light Yellow

Major Application

pharmaceutical small molecule

InChI

InChI=1S/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)

InChIKey

KXPSHSVVYGZKAV-UHFFFAOYSA-N

SMILES

C(OC(=O)C)C(CCN1C2C(N=C1)=C(Cl)N=C(N)N=2)COC(=O)C

LogP

0.92 at 25℃ and pH9.1

CAS DataBase Reference

97845-60-8(CAS DataBase Reference)

9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine Usage And Synthesis

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).

Synthesis

9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine through a four-step synthesis: steps. 1) Preparation of 1,3-diacetoxy-2-bromopropane: 1,3-Dichloro-2-propanol reacts with potassium acetate and ammonium chloride in DMF. After work-up and reaction with triethylamine hydrobromide, distillation yields the product. 2) Preparation of the zinc reagent: 1,3-Diacetoxy-2-bromopropane reacts with zinc powder and anhydrous lithium bromide in THF, initiated by TMSCl. 3) Preparation of the catalyst: Palladium acetate and S-Phos are stirred in THF under nitrogen. 4) Preparation of the final product: 2-Amino-6-chloro-9-bromoethylpurine, the freshly prepared catalyst, and the zinc reagent react in THF. Work-up and recrystallization from ethanol yield the product.

9-(4-Acetoxy-3-acetoxymethylbutyl)-2-amino-6-chloropurine(97845-60-8)Related Product Information

• Betaine
• Acetaminophen
• ALTRENOGEST
• N-Acetylsulfanilyl chloride
• BRL 42222
• Sodium triacetoxyborohydride
• Glycine
• FaMciclovir iMpurity 5
• FaMciclovir Related CoMpound C
• Famciclovir Related Compound A (20 mg) (2-[2-(2-Amino-9H-purin-9-yl)ethyl]propane-1,3-diol hydrochloride)
• FAMCICLOVIR-D4
• Famciclovir N7-Isomer
• Famciclovir
• FaMciclovir iMpurity 7
• Famciclovir Impurity 7
• 9-(4-hydroxybutyl)guanine
• 1,3-Propanediol, 2-[2-(2-amino-6-chloro-9H-purin-9-yl)ethyl]-
• Penciclovir