2-Chloropyrimidine-5-boronic acid pinacol ester

2-Chloropyrimidine-5-boronic acid pinacol ester - Names and Identifiers

Name	2-Chloropyrimidine-5-boronic acid pinacol ester
Synonyms	2-dioxaborolan-2-yl)pyriMidine 2-Chloropyrimidine-5-boronic acid pinacol ester 2-CHLOROPYRIMIDINE-5-BORONIC ACID PINACOL ESTER 2-ChloropyriMidin-5-ylboronic acid pinacol ester 2-(5-Chloro-2-pyrimidyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 2-(2-Chloro-5-pyrimidinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Pyrimidine, 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
CAS	1003845-08-6
InChI	InChI=1S/C10H14BClN2O2/c1-9(2)10(3,4)16-11(15-9)7-5-13-8(12)14-6-7/h5-6H,1-4H3

2-Chloropyrimidine-5-boronic acid pinacol ester - Physico-chemical Properties

Molecular Formula	C10H14BClN2O2
Molar Mass	240.49
Density	1.19±0.1 g/cm3 (20 ºC 760 Torr)
Melting Point	65.0 to 69.0 °C
Boling Point	369.1±15.0 °C(Predicted)
Appearance	Solid
pKa	-1.68±0.22(Predicted)
Storage Condition	Keep in dark place,Sealed in dry,Room Temperature

2-Chloropyrimidine-5-boronic acid pinacol ester - Reference Information

Use

2-chloropyrimidin-5-borate pinacol ester is used to prepare indole derivatives, as a selective Pim kinase inhibitor has a wide range of pharmacological activities. It was also used to prepare TGF-β1 inhibitors and activin A signal transduction. It is a kind of important chemical products and key pharmaceutical and chemical intermediate products.

preparation

borate ester was synthesized from 5-bromo -2-chloropyrimidine in Pd catalytic system with B2(pin)2 as boron reagent at room temperature. the specific synthesis route is shown in the figure below. The research on the synthesis roadmap of pyrimidine -5-boric acid tannol ester shows that pyrimidine -5-boric acid tannol ester is prepared by reacting 5-bromo-2-chloropyrimidine as raw material under 0.5mol%Xphos-Pd-G2 and 0.25mol%Xphos catalytic system with B2(pin)2 as boron reagent, potassium phosphate 7 hydrate as base and ethanol as solvent at room temperature for 1h. The method has the advantages of cheap and easy availability of raw materials, good compatibility of functional groups, mild conditions, simple operation, efficient reaction, and suitable for large-scale preparation.

Last Update：2024-04-09 15:16:37