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

Base Information

• Chemical Name: 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine
• CAS No.: 1052686-60-8
• Molecular Formula: C11H17BN2O3
• Molecular Weight: 236.079
• Hs Code.: 2934999090
• European Community (EC) Number: 856-851-0
• DSSTox Substance ID: DTXSID00702673
• Wikidata: Q72485868
• Mol file: 1052686-60-8.mol

Synonyms:1052686-60-8;2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine;2-Methoxypyrimidin-5-ylboronic acid pinacol ester;SCHEMBL1096510;(2-METHOXYPYRIMIDIN-5-YL)BORONIC ACID PINACOL ESTER;DTXSID00702673;NPIOFBGJGBMTRC-UHFFFAOYSA-N;2-methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine;MFCD13182190;AKOS016012320;DS-6644;SB55514;AM20070703;CS-0041707;EN300-208156;N10621;A849888;F2147-4703;Z2035322146;2-methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidine;2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrimidine;Pyrimidine, 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)

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

Chemical Property:

• Boiling Point: 354.3±34.0 °C(Predicted)
• PKA: 0.94±0.22(Predicted)
• PSA: 53.47000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 0.78440
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 236.1332226
• Heavy Atom Count: 17
• Complexity: 262

Purity/Quality:

99% ^*data from raw suppliers

2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(N=C2)OC
• Use Description: 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine is a versatile compound with applications spanning various fields. In the realm of organic chemistry, it serves as a crucial reagent for Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of a wide range of complex organic compounds, including pharmaceuticals and agrochemicals. This makes it indispensable in drug discovery and development, where it plays a pivotal role in creating novel therapeutic agents. In the field of materials science, this compound is utilized in the synthesis of advanced materials and polymers, contributing to innovations in electronics, photonics, and nanotechnology. Furthermore, in academic research, 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine serves as a valuable tool for investigating reaction mechanisms and conducting studies in synthetic chemistry. Its versatility as a chemical reagent underscores its significance in pharmaceuticals, materials science, and chemical research, driving progress and advancements in these diverse fields.

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

There total 2 articles about 2-Methoxy-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: 98.0%

bis(pinacol)diborane (73183-34-3) + 5-bromo-2-methoxypyrimidine (14001-66-2) → 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (1052686-60-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,2-dimethoxyethane; ethanol; water; toluene; at 85 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.07.103

Reference yield: 38.0%

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8) + 5-bromo-2-methoxypyrimidine (14001-66-2) → 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (1052686-60-8)

Guidance literature:

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane; With potassium methanolate; In 1,2-dimethoxyethane; at 30 ℃; for 0.166667h;

5-bromo-2-methoxypyrimidine; In 1,2-dimethoxyethane; at 30 ℃; for 1h;

DOI:10.1039/c5sc00384a

Reference yield: 72.0%

2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (1052686-60-8) + 5-bromo-4-methoxy-2-nitro-phenylamine (6943-69-7) → 4-methoxy-5-(2-methoxypyrimidin-5-yl)-2-nitroaniline (1052686-66-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; for 6h; Reflux;

DOI:10.1021/jm800318d

upstream raw materials:

bis(pinacol)diborane

5-bromo-2-methoxypyrimidine

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

Downstream raw materials:

4-methoxy-5-(2-methoxypyrimidin-5-yl)-2-nitroaniline

2-fluoro-N-{2-fluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-benzenesulfonamide

(2R,3R)-3-(2-(2-methoxypyrimidin-5-yl)-6,7-dihydrothiazolo[5,4-c]pyridin-5(4H)-yl)-2-(2,4-di-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Refernces

• 1、 Kaiser, Thomas M.,Dentmon, Zackery W.,Burger, Pieter B.,Shi, Qi,Snyder, James P.,Du, Yuhong,Fu, Haian,Liotta, Dennis C.. "Prospective evaluation and success of a machine learning hit-to-lead drug development program against phosphatidylinositol 3-kinase α". . p. 25 - 43. Retrieved 2021/05/28.
• 2、 -. "Pyrrole inhibitors of S-nitrosoglutathione reductase as therapeutic agents". Page/Page column 290. . Retrieved 2015/11/16.