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CS-W001157 4
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4-(5-Bromopyrimidin-2-yl)morpholine

  • CAS No. 84539-22-0

  • Cat. No. CS-0145800
  • Purity≥98%
  • MDL No.MFCD00483251

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

4-(5-Bromopyrimidin-2-yl)morpholine|CS-0145800

Structure of 84539-22-0

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General Information

  • CAS No. 84539-22-0
  • Cat. No. CS-0145800
  • Purity ≥98%
  • MDL No. MFCD00483251
  • Storage 4°C, sealed storage, away from moisture and light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀BrN₃O
  • Molecular Weight 244.09
  • Synonym(s) 5-BROMO-2-MORPHOLIN-1-YL-PYRIMIDINE
  • SMILES BrC1=CN=C(N2CCOCC2)N=C1

Description

4-(5-Bromopyrimidin-2-yl)morpholine features a brominated pyrimidine core linked to a morpholine ring, enabling efficient coupling in cross-coupling reactions. The electron-deficient pyrimidine facilitates nucleophilic substitution, while the morpholine moiety enhances solubility and modulates pharmacophore properties. This combination supports rapid assembly of complex heterocyclic architectures under standard conditions.

Application

4-(5-Bromopyrimidin-2-yl)morpholine serves as a versatile building block in medicinal chemistry, enabling efficient access to pyrimidine-based scaffolds through palladium-catalyzed cross-coupling reactions. The bromine substituent provides high reactivity in Suzuki, Stille, and Buchwald–Hartwig transformations, while the morpholine moiety offers favorable solubility and metabolic stability. Its bench-stable nature and compatibility with diverse functional groups make it ideal for iterative synthesis of targeted heterocyclic compounds.

Synthesis

  • Route1
    • null|null
      110-91-8
    • ~%
    • In-stock
      4-(5-Bromopyrimidin-2-yl)morpholine|CS-0145800
      84539-22-0

    References

    • WO2004/101546 A1, ; Page 34 ;
  • Route2
    • null|null
      110-91-8
    • In-stock
      5-Bromo-2-chloropyrimidine|CS-M1309
      32779-36-5
    • ~80%
    • In-stock
      4-(5-Bromopyrimidin-2-yl)morpholine|CS-0145800
      84539-22-0

    References

    • Epple, Robert; Cow, Christopher; Xie, Yongping; Azimioara, Mihai; Russo, Ross; Wang, Xing; Wityak, John; Karanewsky, Donald S.; Tuntland, Tove; Nguyen-Tran, Van T. B.; Ngo, Cara Cuc; Huang, David; Saez, Enrique; Spalding, Tracy; Gerken, Andrea; Iskandar, Maya; Seidel, H. Martin; Tian, Shin-Shay Journal of Medicinal Chemistry, 2010 , vol. 53, # 1 p. 77 - 105
  • Route3
    • 4-(Pyrimidin-2-yl)morpholine|CS-0155575
      57356-66-8
    • ~93%
    • In-stock
      4-(5-Bromopyrimidin-2-yl)morpholine|CS-0145800
      84539-22-0

    References

    • Paudler, William W.; Jovanovic, Misa V. Journal of Organic Chemistry, 1983 , vol. 48, # 7 p. 1064 - 1069

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   38.25
  • LogP   1.0757
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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