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

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

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 PREPARATION OF AMINO ALCOHOL DERIVATIVES OR SALTS THEREOF

The present invention relates to a process for the preparation of amino alcohol derivatives or salts thereof. In particular the present invention relates to process for the preparation of amino alcohol derivatives or salts thereof which may be used as intermediates in the preparation of HIV reverse transcriptase inhibitors, more preferably Carbovir and Abacavir. The present invention more specifically relates to a process for the preparation of (1S,4R)-4-amino-2-cyclopentene-1-methanol of Formula IIIa. The present invention also specifically relates to process for the preparation of Abacavir sulfate of Formula II using compound of Formula IIIa prepared according to the process of the present invention.

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.

Enantiomer compositions of (1R,4S)-1-butyrylamino-4-(hydroxymethyl)-2-cyclopentene

A novel process for the preparation of (1S,4R)- or (1R,4S)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol of the formulae is described. This entails in the first stage (+/-)-2-azabicyclo[2.2.1]hept-5-en-3-one of the formula being acylated to give a (+/-)-2-azabicyclo[2.2.1]hept-5-en-3-one derivative of the general formula in which R1 denotes C1-4-alkyl, C1-4-alkoxy, aryl or aryloxy, the latter being reduced in the second stage to give a cyclopentene derivative of the general formula in which R1 has the stated meaning, the latter then being converted in the third stage biotechnologically into the (1R,4S)- or (1S,4R)-1-amino-4-(hydroxymethyl)-2-cyclopentene of the formula the latter being converted in the fourth stage with N-(2-amino-4,6-dichloro-5-pyrimidinyl)formamide of the formula into the (1S,4R)- or (1R,4S)-4-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-2-cyclopentene-1-methanol of the formulae and the latter being cyclized in the fifth stage in a known manner to the final product of the formula I or II.

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.

Chloropyrimidine intermediates

The present invention is related to a process of making of 2,6-diaminopurines wherein the 6-amino group is substituted by R4 and R5, by reacting a compound of formula (VI) STR1 with an excess of amine NHR4 R5.