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CS-W001157 4
Total: USD 88.00

5-Bromo-1-methylpyrimidine-2,4(1h,3h)-dione

  • CAS No. 6327-97-5

  • Cat. No. CS-0210282
  • Purity≥98%
  • MDL No.MFCD00038053

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

5-Bromo-1-methylpyrimidine-2,4(1h,3h)-dione|CS-0210282

Structure of 6327-97-5

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General Information

  • CAS No. 6327-97-5
  • Cat. No. CS-0210282
  • Purity ≥98%
  • MDL No. MFCD00038053
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅BrN₂O₂
  • Molecular Weight 205.01
  • Synonym(s) 1-Methyl-5-bromouracil
  • SMILES CN1C=C(Br)C(NC1=O)=O

Description

5-Bromo-1-methylpyrimidine-2,4(1h,3h)-dione features a brominated pyrimidinone core with enhanced electrophilicity at the C5 position. This bench-stable derivative integrates readily into cross-coupling reactions and serves as a key intermediate in medicinal chemistry. The methyl group stabilizes the enol tautomer, improving solubility and handling.

Application

5-Bromo-1-methylpyrimidine-2,4(1H,3H)-dione serves as a versatile building block in medicinal chemistry, enabling efficient functionalization at the C5 position via palladium-catalyzed cross-coupling. Its methyl and carbonyl groups provide enhanced solubility and stability compared to unsubstituted analogs, while the bromine facilitates selective transformations under mild conditions. The pyrimidinedione core is compatible with standard synthetic workflows, offering predictable reactivity for constructing bioactive heterocycles and scaffold diversification.

Synthesis

  • Route1
    • In-stock
      5-Bromouracil|CS-W001982
      51-20-7
    • null|null
      74-88-4
    • ~78%
    • In-stock
      5-Bromo-1-methylpyrimidine-2,4(1h,3h)-dione|CS-0210282
      6327-97-5

    References

    • Shelke, Sandip A.; Sigurdsson, Snorri Th. Nucleic Acids Research, 2012 , vol. 40, # 8 p. 3732 - 3740
  • Route2
    • null|null
      119255-08-2
    • ~78%
    • In-stock
      5-Bromo-1-methylpyrimidine-2,4(1h,3h)-dione|CS-0210282
      6327-97-5

    References

    • Skulski, Lech; Kujawa, Anna; Kujawa, Tadeusz M. Bulletin of the Polish Academy of Sciences, Chemistry, 1987 , vol. 35, # 11-12 p. 499 - 505
  • Route3

    References

    • Tee, Oswald S.; Berks, Charles G. Journal of Organic Chemistry, 1980 , vol. 45, # 5 p. 830 - 835

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   54.86
  • LogP   -0.1639
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   0

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