141271-12-7

Basic information

• Product Name: (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol
• Synonyms: (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol
• CAS NO: 141271-12-7
• Molecular Weight: 255.707
• Mol File: 141271-12-7.mol

Chemical Properties

• Boiling Point: 561.0±60.0 °C(Predicted)
• Density: 1.517±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol(141271-12-7)
• EPA Substance Registry System: (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol(141271-12-7)

Safety Data

• Hazardous Substances Data: 141271-12-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol is used as an impurity in the preparation of Abacavir (A105000) for its role in the development and production of nucleoside reverse transcriptase inhibitors (NRTIs). These inhibitors are crucial in the fight against HIV, as they help to prevent the replication of the virus within the body.
As an impurity in the synthesis of Abacavir, (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol may have implications for the quality, safety, and efficacy of the final drug product. Therefore, its presence is closely monitored and controlled during the manufacturing process to ensure that the therapeutic benefits of Abacavir are not compromised.

Upstream product

• 55583-59-0 2,5-diamino-4,6-dichloropyrimidine 
• 122-51-0 orthoformic acid triethyl ester 
• 168960-18-7 (1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene 
• 168960-19-8 (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride 
• 229613-83-6 (–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride 
• 130931-84-9 (-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride 
• 141271-11-6 (-)-(1S,4R)-4-<(2'-amino-6'-chloropyrimidin-4'-yl)amino>-cyclopent-2-enylmethanol 
• 127061-46-5 methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 
• 130931-86-1 (-)-(1S,4R)-4-acetamidocyclopent-2-enylmethanol 
• 136522-35-5 (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 765-30-0 Cyclopropylamine 
• 171887-04-0 (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene 
• 141271-13-8 (1S,4R)-4-(<2'-amino-6'-chloro-5'-<(4''-chlorophenyl)azo>pyrimidin-4'-yl>amino)cyclopent-2-enylmethanol 

Downstream Products

• 136522-33-3 (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol 

Relevant articles and documents

ANTIVIRAL 4-(2-AMINO-6-HETEROCYLYL-9H-PURIN-9-YL)-2-CYCLOPENTENE-1 -METHANOL COMPOUNDS

The present invention relates to certain antiviral compounds of formula I as defined herein that function as nucleoside reverse transcriptase inhibitors. The present invention also relates to processes for the preparation of these compounds, pharmaceutical compositions comprising them and to their use for the treatment of retroviral infections, and in particular their use in the treatment of HIV-1 virus.

PROCESS FOR THE PREPARATION OF (1S, 4R) -CIS-4-‘2-AMINO-6CHLORO-9H-PURIN-9-YL!-2-CYCLOPENTENE-1-METHANOL

A process for preparing a chloropurine compound of formula (I) or a derivative thereof, which comprises ring closure of the compound of formula (VII) or a derivative thereof in the presence of catalytic acid and at least one equivalent of a formate derivative.

Process for the synthesis of chloropurine intermediates

The present invention relates to a process for the preparation of a carbocyclic purine nucleoside analogue of formula (I), its salts and pharmaceutically acceptable derivatives thereof which comprises hydrolysing a compound of formula (IV) wherein P is a protecting group, in the presence of an acid, condensing the product of formula (V) formed in situ in the presence of a base with a compound of formula (VI) followed by in situ ring closure of the resulting intermediate.

Therapeutic nucleosides

The present invention relates to intermediates useful for the preparation of certain compounds, for example, purine carbocyclic nucleosides.

An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen (1592U89)

Ziagen, (1S, cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2- cyclopentene-1-methanol, was synthesized from (1S,4R)-azabicyclo[2.2.1]hept- 5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4,6-dichloro-5-formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.

Potential Use of Carbocyclic Nucleosides for the Treatment of AIDS: Chemo-enzymatic Syntheses of the Enantiomers of Carbovir

The lactam (1R,4S)-2-azabicyclohept-5-en-3-one , derived by whole cell enantiospecific hydrolysis of the racemate was converted into (-)-carbovir (-)-1 in ten steps.Lipase catalysed acetylation of 4-cis-hydroxycyclopent-2-enylmethyl tripheny