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CS-W001157 4
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5-Bromo-2-(methylthio)pyrimidin-4(3H)-one

  • CAS No. 81560-03-4

  • Cat. No. CS-W022302
  • Molecule weight221.08
  • Purity≥98%
  • MDL No.None

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

5-Bromo-2-(methylthio)pyrimidin-4(3H)-one|CS-W022302

Structure of 81560-03-4

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General Information

  • CAS No. 81560-03-4
  • Cat. No. CS-W022302
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅BrN₂OS
  • Molecular Weight 221.08
  • Synonym(s) 5-bromo-2-methylsulfanyl-3H-pyrimidin-4-one
  • SMILES O=C1NC(SC)=NC=C1Br

Description

5-Bromo-2-(methylthio)pyrimidin-4(3H)-one features a brominated pyrimidinone core with a methylthio substituent at the 2-position, delivering enhanced reactivity for cross-coupling and functionalization. This bench-stable heterocycle integrates readily into synthetic pathways requiring halogen-directed derivatization or metal-catalyzed transformations.

Application

5-Bromo-2-(methylthio)pyrimidin-4(3H)-one serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable bromo substituent. The methylthio group enhances solubility and facilitates selective functionalization, while the pyrimidinone core provides a rigid, hydrogen-bond-capable scaffold suitable for targeted drug discovery. Bench-stable and readily purified by recrystallization, it functions effectively in standard synthetic workflows involving nucleophilic substitution or transition-metal-mediated transformations.

Synthesis

  • Route1

    References

    • Gacek; Undheim 1982 , vol. 36, # 1 B p. 15 - 18

Safety Information

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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

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Computational Chemistry Data

  • TPSA   45.75
  • LogP   1.2543
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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