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4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine

  • CAS No. 944401-55-2

  • Cat. No. CS-0041737
  • Purity≥95%
  • MDL No.MFCD18072554

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

4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine|CS-0041737

Structure of 944401-55-2

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General Information

  • CAS No. 944401-55-2
  • Cat. No. CS-0041737
  • Purity ≥95%
  • MDL No. MFCD18072554
  • Storage -20°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₈BN₃O₂
  • Molecular Weight 235.10
  • Synonym(s) 4-Methyl-2-aminopyrimidine-5-boronic acid pinacol ester
  • SMILES NC1=NC=C(B2OC(C)(C)C(C)(C)O2)C(C)=N1

Description

4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine features a boronate ester group enabling robust Suzuki-Miyaura coupling under mild conditions. The pyrimidine core provides a stable, electron-deficient scaffold for C–N and C–C bond formation. This bench-stable reagent integrates readily into complex molecular architectures with minimal purification requirements.

Application

4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The pyrimidine core provides a robust heterocyclic scaffold with tunable nitrogen functionality, while the pinacol boronate ester enables stable, air-tolerant coupling under mild conditions. This reagent facilitates efficient C–C bond formation in medicinal chemistry and materials synthesis, offering excellent functional group compatibility and straightforward purification by standard chromatographic methods.

Synthesis

  • Route1

    References

    • Genentech, Inc.; Heald, Robert Andrew; McLean, Neville James Patent: US2014/65136 A1, 2014 ; Location in patent: Paragraph 0198; 0199 ;
  • Route2

    References

    • WO2007/84786 A1, ; Page/Page column 92-93 ; WO 2007/084786 A1
  • Route3

    References

    • WO2012/82997 A1, ; WO 2012/082997 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   0.66642
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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