5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

Base Information

• Chemical Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine
• CAS No.: 321724-19-0
• Molecular Formula: C10H15BN2O2
• Molecular Weight: 206.052
• Hs Code.: 2933599090
• European Community (EC) Number: 688-280-6
• DSSTox Substance ID: DTXSID20400624
• Nikkaji Number: J3.349.812H
• Wikidata: Q72504812
• Mol file: 321724-19-0.mol

Synonyms:321724-19-0;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine;Pyrimidine-5-boronic acid pinacol ester;Pinacol ester pyrimidinyl-5-boronic acid;5-Pyrimidineboronic acid pinacol ester;Pyrimidine-5-boronic acid, pinacol ester;5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine;Pyrimidyl-5-boronic acid pinacolate;PYRIMIDYL-5-BORONIC ACID PINACOL ESTER;PYRIMIDINE, 5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;MFCD05155223;PYRIMIDIN-5-YLBORONIC ACID PINACOL ESTER;C10H15BN2O2;SCHEMBL476906;AMY1618;DTXSID20400624;WSRGGSAGSUEJKQ-UHFFFAOYSA-N;AKOS004115215;AC-8557;CS-W019998;PB26151;DS-13712;pyrimidine-5-ylboronic acid pinacol ester;SY004449;5-Pyrimidineboronic acid pinacol ester, 97%;BB 0260161;FT-0600749;T2521;A22860;EN300-132510;J-018667;J-516198;Z1336745113;2-(Pyrimidin-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(5-pyrimidyl)-1,3,2-dioxaborolane;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)pyrimidine;Pyrimidine,5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

Chemical Property:

• Vapor Pressure: 0.0012mmHg at 25°C
• Melting Point: 60-66 °C
• Refractive Index: 1.488
• Boiling Point: 308.9 °C at 760 mmHg
• PKA: 1.63±0.10(Predicted)
• Flash Point: 140.6 °C
• PSA: 44.24000
• Density: 1.07 g/cm³
• LogP: 0.77580
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 206.1226579
• Heavy Atom Count: 15
• Complexity: 224

Purity/Quality:

98% ^*data from raw suppliers

5-PyrimidineboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=CN=C2
• Uses: Pyrimidine-5-boronic acid pinacol ester is used in the preparation of indole derivatives as selective inhibitors of all three members of the Pim kinase family. It is also used to prepare inhibitors of TGF-β1 and activin A signalling. 2-Methoxyphenylborornic Acid Pinacol Ester is used in the preparation of indole derivatives as selective inhibitors of all three members of the Pim kinase family. It is also used to prepare inhibitors of TGF-β1 and activin A signalling.

Technology Process of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

There total 3 articles about 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + pyrimidine 5-boronic acid (109299-78-7) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (321724-19-0)

Guidance literature:

With magnesium sulfate; In toluene; at 20 ℃;

DOI:10.1021/acs.orglett.9b00584

Reference yield: 86.0%

5-bromopyrimidine (4595-59-9) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (321724-19-0)

Guidance literature:

With isopropylmagnesium chloride; In tetrahydrofuran; at -10 - 30 ℃; for 9h;

Reference yield: 14.0%

PYRIMIDINE (289-95-2,25247-63-6) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (321724-19-0)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; In tetrahydrofuran; at 20 ℃; for 25h; Inert atmosphere; Glovebox;

DOI:10.1021/ja412563e

upstream raw materials:

5-bromopyrimidine

bis(pinacol)diborane

PYRIMIDINE

2,3-dimethyl-2,3-butane diol

Downstream raw materials:

N-(2-amino-4,5'-bipyrimidin-6-yl)-N-[3-fluoro-4-(4-pyridinylsulfanyl)phenyl]amine

4-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-6-pyrimidin-5-yl-pyridazin-3-ylamine

(2R,3R)-2-(2,4-difluorophenyl)-3-(2-(pyrimidin-5-yl)-5,6-dihydro[1,2,4]triazolo[1,5-a]piperazine-7(8H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

C₁₈H₁₈N₄O₂

Refernces

• 1、 Wang, Xin,Liu, Wei-Gang,Tung, Chen-Ho,Wu, Li-Zhu,Cong, Huan. "A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions". supporting information. p. 8158 - 8163. Retrieved 2019/09/07.
• 2、 -. "INDOLE AHR INHIBITORS AND USES THEREOF". Paragraph 001138-001139. . Retrieved 2018/11/22.