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CS-W001157 4
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6-Amino-2-oxo-1,2-dihydropyrimidine-5-carbonitrile

  • CAS No. 16462-28-5

  • Cat. No. CS-0074281
  • Purity≥97%
  • MDL No.None

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

6-Amino-2-oxo-1,2-dihydropyrimidine-5-carbonitrile|CS-0074281

Structure of 16462-28-5

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General Information

  • CAS No. 16462-28-5
  • Cat. No. CS-0074281
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄N₄O
  • Molecular Weight 136.11
  • Synonym(s) 4-Amino-2-hydroxypyrimidine-5-carbonitrile
  • SMILES N#CC1=CNC(N=C1N)=O

Description

6-Amino-2-oxo-1,2-dihydropyrimidine-5-carbonitrile features a fused heterocyclic core bearing an amino group at C6 and a nitrile function at C5, enabling direct incorporation into bioactive scaffolds. The electron-deficient pyrimidinone ring facilitates nucleophilic addition and transition-metal-catalyzed coupling reactions. This bench-stable, moisture-tolerant compound serves as a key building block for pharmaceutical intermediates and functional materials.

Application

6-Amino-2-oxo-1,2-dihydropyrimidine-5-carbonitrile serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyrimidine-based scaffolds. Its amino and nitrile functionalities support diverse transformations, including cyclizations, amidations, and metal-catalyzed couplings. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative medicinal chemistry campaigns and process development workflows.

Synthesis

  • Route1
    • null|null
      14048-06-7
    • ~42%
    • In-stock
      6-Amino-2-oxo-1,2-dihydropyrimidine-5-carbonitrile|CS-0074281
      16462-28-5

    References

    • Artigas, Gerard; Marchan, Vicente Journal of Organic Chemistry, 2013 , vol. 78, # 21 p. 10666 - 10677
  • Route2

    References

    • Chatterjee; Anand Journal of Scientific and Industrial Research, 1958 , vol. 17 B, p. 63,68
  • Route3

    References

    • Cilag Patent: US2698326 , 1953 ;

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   95.56
  • LogP   -0.77622
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   0

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