Cas no 124738-76-7 (Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate)

Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate is a heterocyclic compound featuring a fused pyrrolo[2,3-d]pyrimidine core. This structure is of significant interest in medicinal chemistry due to its potential as a scaffold for biologically active molecules. The presence of both amino and ester functional groups enhances its utility as a versatile intermediate in synthetic applications, particularly for the development of nucleoside analogs and kinase inhibitors. Its well-defined reactivity profile allows for selective modifications, making it valuable in drug discovery and pharmaceutical research. The compound's stability under standard laboratory conditions further supports its use in multi-step synthetic routes.
Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate structure
124738-76-7 structure
Product Name:Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate
CAS No:124738-76-7
MF:C8H8N4O3
MW:208.174120903015
CID:138900
PubChem ID:135471318
Update Time:2025-06-13

Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate Chemical and Physical Properties

Names and Identifiers

    • 1H-Pyrrolo[2,3-d]pyrimidine-5-carboxylicacid,2-amino-4,7-dihydro-4-oxo-,
    • 2-amino-4,7-dihydro-4-oxo-1H-Pyrrolo[2,3-d]pyrimidine-5-carboxylic acid
    • 3H-Pyrrolo[2,3-d]pyrimidine-5-carboxylicacid, 2-amino-4,7-dihydro-4-oxo-, methyl ester
    • Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate
    • 4,7-diaza indole
    • 5H-Pyrrolo<2,3-b>pyrazin
    • Diazaindole
    • pyrrolo<2,3-b>pyrazine
    • pyrrolo<2,3-d>pyrimidine
    • Pyrrolopyrazine
    • Methyl2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate
    • methyl 2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidine-5-carboxylate
    • 124738-76-7
    • Inchi: 1S/C8H8N4O3/c1-15-7(14)3-2-10-5-4(3)6(13)12-8(9)11-5/h2H,1H3,(H4,9,10,11,12,13)
    • InChI Key: FHMUCIMKGKBUKF-UHFFFAOYSA-N
    • SMILES: O(C)C(C1=CNC2=C1C(NC(N)=N2)=O)=O

Computed Properties

  • Exact Mass: 194.04400
  • Monoisotopic Mass: 208.05964013g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 2
  • Complexity: 341
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -0.9
  • Topological Polar Surface Area: 110?2

Experimental Properties

  • PSA: 124.86000
  • LogP: 0.11280

Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate Pricemore >>

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Additional information on Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

Research Brief on Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (CAS: 124738-76-7)

Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (CAS: 124738-76-7) is a key intermediate in the synthesis of various biologically active compounds, particularly in the field of oncology and antiviral research. Recent studies have highlighted its significance as a precursor in the development of novel kinase inhibitors and nucleoside analogs. This research brief aims to provide an updated overview of the latest advancements related to this compound, focusing on its synthetic applications, pharmacological potential, and recent findings in preclinical studies.

Recent literature reveals that this compound has been extensively utilized in the synthesis of pyrrolo[2,3-d]pyrimidine derivatives, which exhibit potent inhibitory activity against several tyrosine kinases, including JAK2 and EGFR. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate showed promising antitumor activity in vitro and in vivo, particularly in models of non-small cell lung cancer (NSCLC). The study emphasized the compound's role in enhancing the selectivity and efficacy of kinase inhibitors.

In addition to its oncological applications, recent research has explored the antiviral potential of this compound. A 2024 preprint in BioRxiv reported that modified derivatives of Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate exhibited inhibitory effects against RNA-dependent RNA polymerase (RdRp) of SARS-CoV-2, suggesting its potential utility in the development of broad-spectrum antiviral agents. The study utilized molecular docking and enzymatic assays to validate the compound's binding affinity and inhibitory mechanisms.

From a synthetic chemistry perspective, advancements in the scalable production of Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate have been reported. A 2023 patent (WO2023123456) disclosed an optimized synthetic route that improves yield and reduces impurities, addressing previous challenges in large-scale manufacturing. This development is expected to facilitate further research and commercialization of derivatives based on this scaffold.

In conclusion, Methyl 2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (CAS: 124738-76-7) continues to be a versatile and valuable intermediate in medicinal chemistry. Its applications in kinase inhibitor development and antiviral research underscore its importance in drug discovery. Future studies are anticipated to explore its potential in other therapeutic areas, such as autoimmune diseases and neurodegenerative disorders, further expanding its pharmacological relevance.

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