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
• Article Data: 7

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

4-(2,5-Diamino-6-chloropyrimidin-4-ylamino)cyclopent-2-enyl]methanol) is an impurity in the preparation of Abacavir (A105000), a nucleoside reverse transcriptase inhibitor (NRTI) (1,2,3).

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 
• 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 
• 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 
• 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 

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 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.

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.