171887-04-0

Basic information

• Product Name: N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide
• Synonyms: N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide;N-(2-Amino-4-chloro-6-(((1R,4S)-4-(hydroxymethyl)-cyclopent-2-en-1-yl)amino)pyrimidin-5-yl)formam;N-[2-Amino-4-chloro-6-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enylamino]pyrimin-5-yl]formamide;(1R-cis)-N-[2-amino-4-chloro-6-[[4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]-formamide;N-(2-Amino-4-chloro-6-(((1R,4S)-4-(hydroxymethyl)-cyclopent-2-en-1-yl)amino)pyrimidin-5-yl)for;(1S,4R)-4-[(2-Amino-6-chloro-5-formamide-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol
• CAS NO: 171887-04-0
• Molecular Formula: C₁₁H₁₄ClN₅O₂
• Molecular Weight: 284
• EINECS: 1312995-182-4
• Mol File: 171887-04-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 675.0±65.0 °C(Predicted)
• Appearance: white-off powder or granule
• Density: 1.550
• Storage Temp.: 2-8°C
• PKA: 11.47±0.70(Predicted)
• CAS DataBase Reference: N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide(171887-04-0)
• EPA Substance Registry System: N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide(171887-04-0)

Safety Data

• Hazardous Substances Data: 171887-04-0(Hazardous Substances Data)

Usage

Description

N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide is a complex organic compound with a unique molecular structure. It is characterized by its amino, chloro, and hydroxymethyl groups, as well as its formamide and pyrimidinyl moieties. N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide serves as a crucial intermediate in the pharmaceutical industry due to its potential applications in the development of therapeutic agents.

Uses

Used in Pharmaceutical Industry:
N-[2-Amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinyl]formamide is used as an intermediate in the synthesis of the HIV reverse transcriptase inhibitor Ziagen (also known as Abacavir). This application is significant because it plays a vital role in the development of antiretroviral drugs that help combat the Human Immunodeficiency Virus (HIV) and its progression to Acquired Immunodeficiency Syndrome (AIDS).
As an intermediate in the synthesis of Ziagen, this compound contributes to the production of a medication that has been proven effective in treating HIV by inhibiting the viral reverse transcriptase enzyme, which is essential for the replication of the virus. By incorporating this compound into the synthesis process, researchers and pharmaceutical companies can develop and manufacture life-saving medications for patients suffering from HIV and AIDS.

Upstream product

• 136522-35-5 (1R,4S)-1-amino-4-hydroxymethyl-2-cyclopentene 
• 171887-03-9 N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 171887-02-8 2-amino-5-{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine 
• 168960-19-8 (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride 
• 229177-52-0 ((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 

Downstream Products

• 141271-12-7 (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol 
• 136470-78-5 abacavir 
• 172015-79-1 ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride 

Relevant articles and documents

Abacavir intermediate and method for purifying same

The invention discloses an abacavir intermediate and a method for purifying the same. The method includes heating mixtures with abacavir intermediate crude products, purified water and water-soluble organic solvents until the abacavir intermediate crude products are completely dissolved so as to obtain mixed liquid; carrying out cooling and crystallization treatment on the mixed liquid; carrying out filtering and drying treatment after crystallization treatment is carried out so as to obtain abacavir intermediate pure products. A structural formula of the abacavir intermediate is shown as a formula IV. The abacavir intermediate and the method have the advantage that the method is easy and convenient to implement and is suitable for industrial production.

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.