2-AMINOPYRIMIDINE-5-BORONIC ACID, PINACOL ESTER

Base Information

• Chemical Name: 2-AMINOPYRIMIDINE-5-BORONIC ACID, PINACOL ESTER
• CAS No.: 402960-38-7
• Molecular Formula: C10H16BN3O2
• Molecular Weight: 221.067
• Hs Code.: 2934999090
• Mol file: 402960-38-7.mol

Synonyms:(2-Aminopyrimidin-5-yl)boronic acid pinacol ester;2-(2-Aminopyrimidin-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2-amine;[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrimidin-2-yl]amine;

Chemical Property of 2-AMINOPYRIMIDINE-5-BORONIC ACID, PINACOL ESTER

Chemical Property:

• Melting Point: 209-211 °C
• Boiling Point: 394.8 °C at 760 mmHg
• PKA: 3.66±0.10(Predicted)
• Flash Point: 192.6 °C
• PSA: 70.26000
• Density: 1.13 g/cm³
• LogP: 0.93920
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly, Heated)
• Water Solubility.: Slightly soluble in water. Soluble in chloroform.

Purity/Quality:

98% ^*data from raw suppliers

2-Aminopyrimidine-5-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xi,Xn,T
• Statements: 36/37/38-22-25
• Safety Statements: 26-36/37/39-36/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Aminopyrimidine-5-boronic Acid Pinacol Ester is used in the preparation of phosphoinositide-3-kinases (PI3K) inhibitors.

Technology Process of 2-AMINOPYRIMIDINE-5-BORONIC ACID, PINACOL ESTER

There total 5 articles about 2-AMINOPYRIMIDINE-5-BORONIC ACID, PINACOL ESTER 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: 90.0%

5-bromo-2-aminopyrimidine (7752-82-1) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyrimidin-2-ylamine (402960-38-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; at 110 ℃; for 4h;

Reference yield: 74.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + Trimethyl borate (121-43-7,63156-11-6) + benzhydrylidene-(5-bromo-pyrimidine-2-yl)amine (1072850-89-5) → 5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyrimidin-2-ylamine (402960-38-7)

Guidance literature:

benzhydrylidene-(5-bromo-pyrimidine-2-yl)amine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

Trimethyl borate; In tetrahydrofuran; hexane; at -85 ℃; for 1h;

2,3-dimethyl-2,3-butane diol; With sodium hydroxide; sulfuric acid; more than 3 stages;

Reference yield: 52.0%

→ 5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyrimidin-2-ylamine (402960-38-7)

Guidance literature:

upstream raw materials:

5-bromo-2-aminopyrimidine

bis(pinacol)diborane

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

Trimethyl borate

Downstream raw materials:

5-(4-(trifluoromethyl)phenyl)pyrimidin-2-amine

Refernces

• 1、 Patel, Nitinchandra D.,Zhang, Yongda,Gao, Joe,Sidhu, Kanwar,Lorenz, Jon C.,Fandrick, Keith R.,Mulder, Jason A.,Herbage, Melissa A.,Li, Zhibin,Ma, Shengli,Lee, Heewon,Grinberg, Nelu,Song, Jinhua J.,Busacca, Carl A.,Yee, Nathan K.,Senanayake, Chris H.. "Development of an Efficient Synthesis of (2-Aminopyrimidin-5-yl) Boronic Acid". . p. 95 - 99. Retrieved 2016.
• 2、 -. "Transition metal complex, polymer, mixture, composition and organic electronic device". Paragraph 0217-0220; 0336-0339. . Retrieved 2020/05/01.