2-CHLOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER Chemical Properties

Melting point:

65.0 to 69.0 °C

Boiling point:

369.1±15.0 °C(Predicted)

Density 

1.19±0.1 g/cm3 (20 ºC 760 Torr)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Solid

pka

-1.68±0.22(Predicted)

color 

White to Yellow to Orange

Safety Information

HS Code 

2933599590

2-CHLOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER Usage And Synthesis

Uses

Pinacol 2-chloropyrimidine-5-boronate is used to prepare indole derivatives, exhibiting broad pharmacological activity as a selective Pim kinase inhibitor. It is also used to prepare TGF-β1 inhibitors and activin A signal transducers. It is an important chemical product and a key pharmaceutical intermediate.

Synthesis

34). General procedure for the synthesis of 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidines: to a mixture of toluene (16 mL) and THF (4 mL) containing 5-bromo-2-chloropyrimidine (10 mmol, 1.93 g) and triisopropyl borate (12 mmol, 2.8 mL) at -78 °C, over a period of Hexane (1.58 M, 12 mmol, 7.6 mL) was added slowly and dropwise over 45 min. The reaction mixture was continued to be stirred at -78 °C for 1 hour. Subsequently, the mixture was slowly warmed to -20 °C and 1 M aqueous hydrochloric acid (20 mL) was added. After continued warming to room temperature, the precipitate was collected and washed with hexane to give a colorless powder (808 mg, 51% yield). A mixture of this powder (3.63 mmol, 575 mg), pinacol (3.81 mmol, 450 mg), and magnesium sulfate (18.15 mmol, 2.2 g) in toluene (10 mL) was stirred at room temperature for 15 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting solid was washed with water to afford the target product 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidine (875 mg, quantitative yield); ESI-MS m/z: 159 [M + 1 - pinacol], retention time 1.75 min (condition A).

References

[1] Patent: WO2008/9435, 2008, A1. Location in patent: Page/Page column 189-190
[2] Patent: US2009/118287, 2009, A1. Location in patent: Page/Page column 67-68

2-CHLOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER(1003845-08-6)Related Product Information

• 2,4,5-Trichloropyrimidine
• 2-CHLORO-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE
• 2-FLUOROPHENYLBORONIC ACID, PINACOL ESTER
• 2-(4-BroMo-2,6-difluoro-phenyl)-4,4,5,5-tetraMethyl-[1,3,2]dioxaborolane
• 1-(3-Methoxypropyl)-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
• 1-BENZYL-1,2,3,6-TETRAHYDROPYRIDINE-4-BORONIC ACID PINACOL ESTER
• 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1,2,3,6-tetrahydropyridine
• 2-(3-BroMo-2-fluoro-phenyl)-4,4,5,5-tetraMethyl-[1,3,2]dioxaborolane
• 1-Isopropyl-1H-pyrazole-5-boronic acid, pinacol ester