1500-85-2 | 4-Amino-7H-pyrrolo[2,3-d]pyrimidine

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$7.00	$5.00
5g	98%	in stock	$24.00	$17.00
10g	98%	in stock	$42.00	$30.00
25g	98%	in stock	$54.00	$38.00

Description

• Catalog Number: AA75248
• Chemical Name: 4-Amino-7H-pyrrolo[2,3-d]pyrimidine
• CAS Number: 1500-85-2
• Molecular Formula: C6H6N4
• Molecular Weight: 134.1386
• MDL Number: MFCD01686848
• SMILES: Nc1ncnc2c1cc[nH]2

Computed Properties

• Complexity: 127
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• XLogP3: 0.3

Upstream Synthesis Route

4-Amino-7H-Pyrrolo[2,3-d]Pyrimidine, a versatile chemical compound, plays a crucial role in various chemical synthesis processes. This compound is commonly used as a building block in the production of pharmaceuticals, agrochemicals, and advanced materials due to its unique structural properties. In chemical synthesis, 4-Amino-7H-Pyrrolo[2,3-d]Pyrimidine serves as a key intermediate in the creation of complex organic molecules, facilitating the formation of diverse functional groups and molecular structures. Its reactivity and compatibility with a wide range of reagents make it a valuable tool for the preparation of novel compounds with potential applications in medicinal chemistry, materials science, and other research areas. The incorporation of 4-Amino-7H-Pyrrolo[2,3-d]Pyrimidine into synthetic pathways enables chemists to access a wide spectrum of molecular architectures and explore new avenues for the development of innovative products and technologies.

Literature

• First total synthesis of a naturally occurring iodinated 5'-deoxyxylofuranosyl marine nucleoside.

  Marine drugs 20120401

• Influence of the nucleobase and anchimeric assistance of the carboxyl acid groups in the hydrolysis of amino acid nucleoside phosphoramidates.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20120116

• Anthraquinone as a redox label for DNA: synthesis, enzymatic incorporation, and electrochemistry of anthraquinone-modified nucleosides, nucleotides, and DNA.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20111209

• Increasing the speed limit for hole transport in DNA.

  Journal of the American Chemical Society 20110803

• Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates: synthesis, polymerase incorporation to DNA and electrochemical study.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20110516

• Synthesis of acetylene linked double-nucleobase nucleos(t)ide building blocks and polymerase construction of DNA containing cytosines in the major groove.

  The Journal of organic chemistry 20110506

• Azide-alkyne 'click' conjugation of 8-aza-7-deazaadenine-DNA: synthesis, duplex stability, and fluorogenic dye labeling.

  Bioconjugate chemistry 20100915

• Direct voltammetric analysis of DNA modified with enzymatically incorporated 7-deazapurines.

  Analytical chemistry 20100815

• Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family.

  Journal of medicinal chemistry 20091008

• Probing RNA conformational dynamics and heterogeneity using femtosecond time-resolved fluorescence spectroscopy.

  Methods (San Diego, Calif.) 20091001

• Sequence-independent and rapid long-range charge transfer through DNA.

  Nature chemistry 20090501

• Genome-scale reconstruction of Escherichia coli's transcriptional and translational machinery: a knowledge base, its mathematical formulation, and its functional characterization.

  PLoS computational biology 20090301

• Synthesis and photophysical properties of 7-deaza-2'-deoxyadenosines bearing bipyridine ligands and their Ru(II)-complexes in position 7.

  Organic & biomolecular chemistry 20080821

• Formation of purine-purine mispairs by Sulfolobus solfataricus DNA polymerase IV.

  Biochemistry 20080805

• Minisequencing with acyclonucleoside triphosphates tethered to lanthanide(III) chelates.

  Bioconjugate chemistry 20080601

• Oligodeoxynucleotides containing 3-bromo-3-deazaadenine and 7-bromo-7-deazaadenine 2'-deoxynucleosides as chemical probes to investigate DNA-protein interactions.

  Chembiochem : a European journal of chemical biology 20080215

• Hoogsteen vs. Watson-Crick base pairing: incorporation of 2-substituted adenine- and 7-deazaadenine 2'-deoxy-beta-D-ribonucleosides into oligonucleotides.

  Chemistry & biodiversity 20071201

• An efficient method for the construction of functionalized DNA bearing amino acid groups through cross-coupling reactions of nucleoside triphosphates followed by primer extension or PCR.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

• Structure of purine-purine mispairs during misincorporation and extension by Escherichia coli DNA polymerase I.

  Biochemistry 20060321

• 7-deazapurin-2,6-diamine and 7-deazaguanine: synthesis and property of 7-substituted nucleosides and oligonucleotides.

  Nucleosides, nucleotides & nucleic acids 20050101

• Probing the solvent accessibility and electron density of adenine: oxidation of 7-deazaadenine in bent DNA and purine doublets.

  Inorganic chemistry 20040126

• Thermodynamic stability and structural features of the J4/5 loop in a Pneumocystis carinii group I intron.

  Biochemistry 20031209

• DNA sequence recognition by the antitumor drug ditercalinium.

  Biochemistry 20020709

• Toward electrochemical resolution of two genes on one electrode: using 7-deaza analogues of guanine and adenine to prepare PCR products with differential redox activity.

  Analytical chemistry 20020115

• 2-Amino-7-deazaadenine forms stable base pairs with cytosine and thymine.

  Bioorganic & medicinal chemistry letters 20020107

• Phosphoramidites and oligonucleotides containing 7-deazapurines and pyrimidines carrying aminopropargyl side chains.

  Nucleosides, nucleotides & nucleic acids 20010101

• Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.

  Biochemical pharmacology 19951109