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Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-carboxylate

  • CAS No. 1610705-51-5

  • Cat. No. CS-0054482
  • Purity≥97%
  • MDL No.None

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

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-carboxylate|CS-0054482

Structure of 1610705-51-5

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General Information

  • CAS No. 1610705-51-5
  • Cat. No. CS-0054482
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₇BN₂O₄
  • Molecular Weight 264.09
  • Synonym(s) Methyl pyrimidine-5-boronic acid pinacol ester-2-carboxylate
  • SMILES O=C(C1=NC=C(B2OC(C)(C)C(C)(C)O2)C=N1)OC

Description

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-carboxylate features a boronate ester group that enables efficient Suzuki-Miyaura coupling under mild conditions. The tetramethyl-substituted dioxaborolane enhances stability and solubility in organic solvents. This reagent integrates readily into complex molecular architectures with high functional group tolerance.

Application

Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-carboxylate serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pyrimidine core enables access to bioactive heterocycles, while the tetramethylborolane group provides excellent stability, low toxicity, and compatibility with diverse functional groups. This reagent facilitates efficient C–C bond formation under mild conditions, offering reliable yields and simplified purification—ideal for iterative synthesis in medicinal chemistry and process development workflows.

Safety Information

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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

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Computational Chemistry Data

  • TPSA   70.54
  • LogP   0.5624
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   2

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