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Methyl 5-aminopyrimidine-2-carboxylate

  • CAS No. 73418-88-9

  • Cat. No. CS-0049006
  • Purity≥95%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

Methyl 5-aminopyrimidine-2-carboxylate|CS-0049006

Structure of 73418-88-9

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General Information

  • CAS No. 73418-88-9
  • Cat. No. CS-0049006
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₇N₃O₂
  • Molecular Weight 153.14
  • Synonym(s) 2-Pyrimidinecarboxylicacid,5-amino-,methylester(9CI)
  • SMILES COC(=O)C1=NC=C(N)C=N1

Description

Methyl 5-aminopyrimidine-2-carboxylate features a pyrimidine core bearing both amino and ester functionalities, enabling direct incorporation into heterocyclic scaffolds. The para-amino group enhances electron density for downstream coupling, while the methyl ester facilitates selective hydrolysis or derivatization under standard conditions. This bench-stable compound serves as a key intermediate in the synthesis of bioactive nucleoside analogs and kinase inhibitors.

Application

Methyl 5-aminopyrimidine-2-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient access to pyrimidine-based scaffolds. The amino and ester functionalities offer orthogonal reactivity for downstream modifications, including amide coupling, nucleophilic substitution, and metal-catalyzed cross-coupling reactions. Its bench-stable nature and compatibility with standard purification methods make it well-suited for multi-step synthesis workflows in API development.

Synthesis

  • Route1
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    • ~%
    • In-stock
      Methyl 5-aminopyrimidine-2-carboxylate|CS-0049006
      73418-88-9

    References

    • Pfizer Inc. Patent: US2012/165343 A1, 2012 ; Location in patent: Page/Page column 62 ;
  • Route2

    References

    • Pfizer Inc. Patent: US2012/165343 A1, 2012 ;
  • Route3
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      56622-06-1
    • ~%
    • In-stock
      Methyl 5-aminopyrimidine-2-carboxylate|CS-0049006
      73418-88-9

    References

    • Ohta, Kiminori; Kawachi, Emiko; Inoue, Noriko; Fukasawa, Hiroshi; Hashimoto, Yuichi; Itai, Akiko; Kagechika, Hiroyuki Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 10 p. 1504 - 1513

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   78.1
  • LogP   -0.1546
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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