104227-86-3

Basic information

• Product Name: 2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL
• Synonyms: 2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL;6-DEOXY PENCICLOVIR;DI-DESACETYL FAMCICLOVIR;DidesacetylFamciclovir,BRL42359;1,3-Propanediol, 2-(2-(2-amino-9H-purin-9-yl)ethyl)-;BRL 42359;2-(2-(2-AMino-9H-purin-9-yl)ethyl)propane-1,3-diol;Famciclovir USP RC A
• CAS NO: 104227-86-3
• Molecular Formula: C₁₀H₁₅N₅O₂
• Molecular Weight: 237.26
• Product Categories: Various Metabolites and Impurities;Bases & Related Reagents;Intermediates & Fine Chemicals;Metabolites;Nucleotides;Pharmaceuticals
• Mol File: 104227-86-3.mol

Chemical Properties

• Melting Point: 156-158°C
• Boiling Point: 594.3 °C at 760 mmHg
• Flash Point: 313.2 °C
• Appearance: /
• Density: 1.55 g/cm³
• Vapor Pressure: 5.73E-15mmHg at 25°C
• Refractive Index: 1.718
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 14.40±0.10(Predicted)
• CAS DataBase Reference: 2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL(104227-86-3)
• EPA Substance Registry System: 2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL(104227-86-3)

Safety Data

• Hazardous Substances Data: 104227-86-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL is used as an antiviral agent for the treatment of viral infections. It is a key metabolite of Famciclovir, which helps in inhibiting the replication of viruses, thus providing relief from symptoms and preventing the spread of infections.
Used in Chemical Industry:
2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL is used as a raw material in the synthesis of various chemical compounds. Its unique structure allows it to be a versatile building block for the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Cosmetic Industry:
2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL is used as a humectant in cosmetic formulations. Its ability to retain moisture makes it an effective ingredient in skincare products, helping to maintain skin hydration and improve overall skin health.
Used in Food Industry:
2-[2-(2-AMINO-9H-PURIN-9-YL)ETHYL]-1,3-PROPANEDIOL is used as a sweetener and humectant in the food industry. Its sweetening properties, combined with its ability to retain moisture, make it a valuable ingredient in various food products, enhancing taste and texture while extending shelf life.

InChI:InChI=1/C10H15N5O2/c11-10-12-3-8-9(14-10)15(6-13-8)2-1-7(4-16)5-17/h3,6-7,16-17H,1-2,4-5H2,(H2,11,12,14)

Upstream product

• 104227-87-4 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine 
• 104227-89-6 5-[2-(2-aminopurin-9-yl)ethyl]-2,2-dimethyl-1,3-dioxane 
• 17495-12-4 2-amino-7-benzyl-1H-purin-6(7H)-one 
• 19962-37-9 N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide 
• 118-00-3 G 
• 97845-72-2 2-[(acetyloxy)methyl]-4-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)butyl acetate 
• 7459-46-3 triethyl 1,1,2-ethanetricarboxylate 
• 97845-59-5 2-amino-6-chloro-9-<2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl>purine 
• 97845-60-8 9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine 
• 144-55-8 sodium hydrogencarbonate 
• 172529-94-1 2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine 
• 1033329-78-0 C₁₀H₁₇N₅O₃ 
• 122497-22-7 diethyl 2-(2-(2-aminopurine-9-yl)ethyl)malonate 
• 10310-21-1 2-Amino-6-chloropurin 

Downstream Products

• 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 
• 120687-07-2 (R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine 
• 247081-81-8 2-amino-9-(3-acetoxymethyl-4-isopropoxycarbonyloxybut-1-yl)purine 
• 120687-10-7 (R,S)-2-amino-9-<4-(benzyloxy)-3-(hydroxymethyl)but-1-yl>purine 

Relevant articles and documents

Method for synthesizing famciclovir by using microchannel reactor

The invention discloses a preparation method for synthesizing famciclovir by using a microchannel reactor, which comprises the following steps: mixing and dispersing 2-amino-6-chloro-9-(4-hydroxy-3-hydroxymethylbutyl) purine serving as a raw material and a palladium-carbon catalyst in a solvent, feeding by using a slurry pump, and performing dechlorination reaction with hydrogen in a microchannel continuous flow reactor to obtain reaction liquid, filtering the obtained reaction liquid, respectively inputting the filteringed reaction liquid and an acetic anhydride solution into the microchannel continuous flow reactor by using a diaphragm feeding pump, and carrying out esterification reaction in the microchannel reactor to obtain famciclovir. Compared with the prior art, the method has the advantages that the process safety can be greatly improved by carrying out hydrogenation reaction in the micro-channel continuous flow reactor; as the microchannel continuous flow reactor has the characteristic of high-efficiency mass and heat transfer, the reaction time can be effectively shortened, the use amount of raw materials is reduced, and the discharge of three wastes is reduced; and the route of first hydrogenation and then esterification is adopted, so that hydrolysis of ester bonds during first esterification and then hydrogenation can be effectively avoided, and the product purity is improved.

A new method to synthesize famciclovir

A new and efficient method has been reported for the synthesis of 2-amino-9-[4-acetoxy-3-(acetoxymethyl)butyl-1-yl]purine(famciclovir)starting from guanine. The route involves chlorination of guanine, optimized Mitsunobu reaction, coupling with diethyl malonate, hydrogenation, reduction and esterification,and the overall yield is about 29%. This method does not require any form of chromatographic purification to give pure famciclovir, and it is an industrially viable manufacturing process for this drug. The Japan Institute of Heterocyclic Chemistry.

AN IMPROVED PROCESS FOR THE PREPARATION OF PURINE DERIVATIVE

The present invention provides an improved process for the preparation of purine derivative of Formula I.

AN IMPROVED PROCESS FOR PREPARING PURINE DERIVATIVE

A process for the preparation of famciclovir a compound of Formula (I) and its intermediates.

Preparation of famciclovir and other purine derivatives

Purine derivatives, substituted at the 9-position, are prepared from a chloro substituted purine starting material, first making an alkyl substitution at the 9-position, then forming the desired esterified side chain, reducing this and hydrogenating the resultant diol prior to addition of alkyl carbonyl groups.

PROCESS FOR THE PREPARATION OF FAMCICLOVIR

The invention provides processes for making famciclovir with low levels of undesirable by-products. The present invention discloses a process comprises reacting a compound of formula I (acetic acid 2-acetoxymethyl-4-(5-amino-7-chloro-imidazo [4,5-b]pyridin-3-yl)-butyl ester) in the presence of a palladium on charcoal catalyst in a C1-C6 alkyl acetate and ammonium formate. The present invention further discloses a process comprises reacting a compound of formula I (acetic acid 2-- acetoxymethyl-4-(5-amino-7-chloro-imidazo[4,5-b]pyridin-3-yl)-butyl ester) in the presence of a palladium on charcoal catalyst in a mixture of a C1-C6 alkyl acetate, a C1-C4 alcohol and ammonium formate.

Regioselective functionalization of guanine: Simple and practical synthesis of 7- and 9-alkylated guanines starting from guanosine

Reaction of N2-acetyl-9- and/or -7-benzylated guanines 8 and 12 with selected alkylating agents in 1-methyl-2-pyrrolidone at 120°C yielded the guaninium salts 9 and 13. The salts were consequently transformed by phase transfer hydrogenation into N7- and N9-isomers 10 and 14, respectively, in a highly regioselective manner. A convenient deoxygenation of both derivatives, achieved via the corresponding O6-arenesulfonates, into 2-aminopurine potential prodrugs was also established.

Purine derivatives having cyclopropane ring

The present invention is directed to a process for preparing a cyclopropane ring-cleaved purine derivative represented by the following formula: comprising hydrogenating a purine derivative having a cyclopropane ring represented by the following formula:

Purine derivatives having cyclopropane ring

A purine derivative having a cyclopropane ring represented by the formula (I): wherein A is -CH2- group or -CO- group; X1 is hydrogen atom, a halogen atom, an alkoxy group having 1 to 10 carbon atoms, or hydroxyl group; each of X2, X3, and X4 is independently hydrogen atom or a halogen atom; R1 is hydrogen atom, a halogen atom, or a protected or unprotected amino group; and each of R2 and R3 is independently hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 7 carbon atoms, a substituted or unsubstituted aralkyl group, having 7 to 11 carbon atoms, or a substituted or unsubstituted acyl group having 1 to 7 carbon atoms, with proviso that in a case where A is -CO- group, neither R2 nor R3 is a substituted or unsubstituted acyl group having 1 to 7 carbon atoms, and each of X3 and X4 is independently a halogen atom, and a process for preparing the same.

A direct approach to the synthesis of famciclovir and penciclovir

Reaction of 2-amino-6-chloropurine with triethyl 3-bromopropane-1,1,1- tricarboxylate followed by decarbethoxylation/transsesterification of the unpurified product was the key sequence in sythesising both the anti- herpesvirus agent penciclovir and its form famciclovir in three isolated steps.