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CS-W001157 4
Total: USD 88.00

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyrimidin-2-amine

  • CAS No. 944401-58-5

  • Cat. No. CS-0041141
  • Purity≥97%
  • MDL No.MFCD09952051

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

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyrimidin-2-amine|CS-0041141

Structure of 944401-58-5

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General Information

  • CAS No. 944401-58-5
  • Cat. No. CS-0041141
  • Purity ≥97%
  • MDL No. MFCD09952051
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₅BF₃N₃O₂
  • Molecular Weight 289.06
  • Synonym(s) 2-Amino-4-Trifluoropyrimidine-5-Boronic Acid Pinacol Ester
  • SMILES NC1=NC=C(B2OC(C)(C)C(C)(C)O2)C(C(F)(F)F)=N1

Description

This boronate-functionalized pyrimidine amine features a stable tetramethylboronate group enabling efficient Suzuki-Miyaura coupling under mild conditions. The electron-deficient pyrimidine core pairs with the trifluoromethyl substituent to enhance reactivity and metabolic stability, making it ideal for constructing complex heterocyclic architectures in medicinal chemistry and materials science.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)pyrimidin-2-amine serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. Its trifluoromethylpyrimidine core enables efficient construction of biologically relevant heterocyclic scaffolds, while the stable tetramethylboronate group facilitates mild reaction conditions, excellent functional group tolerance, and straightforward purification. This reagent is well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • WO2008/98058 A1, ; Page/Page column 63-64 ; WO 2008/098058 A1
  • Route2

    References

    • NOVARTIS AG; Fairhurst, Robin Alec; Furet, Pascal; Kalthoff, Frank Stephan; Lerchner, Andreas; Rueeger, Heinrich Patent: US2014/135330 A1, 2014 ; Location in patent: Paragraph 0218 ;
  • Route3

    References

    • US2013/225574 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-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   70.26
  • LogP   1.3768
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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