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CS-W001157 4
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1-(2-Fluoro-6-(trifluoromethyl)benzyl)-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione

  • CAS No. 1150560-54-5

  • Cat. No. CS-0052664
  • Purity≥97%
  • MDL No.None

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

1-(2-Fluoro-6-(trifluoromethyl)benzyl)-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione|CS-0052664

Structure of 1150560-54-5

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General Information

  • CAS No. 1150560-54-5
  • Cat. No. CS-0052664
  • Purity ≥97%
  • MDL No. None
  • Storage RT, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₉F₄IN₂O₂
  • Molecular Weight 428.12
  • Synonym(s) elagolix intermediate 5
  • SMILES CC1=C(I)C(=O)NC(=O)N1CC1=C(C=CC=C1F)C(F)(F)F

Description

This fluorinated pyrimidinedione integrates a trifluoromethyl group and iodine substituent, enabling direct functionalization in late-stage diversification. The 2-fluoro-6-(trifluoromethyl)benzyl moiety enhances metabolic stability and lipophilicity, while the iodo handle facilitates cross-coupling reactions under standard conditions.

Application

1-(2-Fluoro-6-(trifluoromethyl)benzyl)-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione serves as a versatile building block for the synthesis of substituted pyrimidinediones, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling. The iodide group facilitates reliable coupling with diverse nucleophiles, while the trifluoromethyl and fluorinated aromatic moieties provide enhanced metabolic stability and lipophilicity—key attributes in medicinal chemistry. Bench-stable and compatible with standard purification methods, it functions effectively in multistep synthetic sequences targeting bioactive heterocycles.

Synthesis

  • Route1

    References

    • NEUROCRINE BIOSCIENCES, INC. Patent: WO2009/62087 A1, 2009 ; Location in patent: Page/Page column 8-9 ; WO 2009/062087 A1

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-P280-P302+P352

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Computational Chemistry Data

  • TPSA   54.86
  • LogP   2.65582
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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