628692-15-9

Usage

Chemical Properties

Off-white to light yellow solid

InChI:InChI=1/C5H7BN2O3/c1-11-5-7-2-4(3-8-5)6(9)10/h2-3,9-10H,1H3

Upstream product

• 121-43-7 Trimethyl borate 
• 14001-66-2 5-bromo-2-methoxypyrimidine 

Downstream Products

• 1023327-92-5 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(2-methoxypyrimidin-5-yl)-pyridin-2-amine 
• 1186110-91-7 1-ethyl-3-(5-(2-methoxypyrimidin-5-yl)-4-(4-phenylthiazol-2-yl)pyridin-2-yl)urea 
• 1205685-03-5 5-{[1-(2-chloro-3-fluoro-4-methoxyphenyl)-2-(methoxymethyl)-3,3,3-trifluoro-2-hydroxypropyl]amino}-7-fluoro-1-(2-methoxypyrimidine-5-yl)-1H-quinolin-2-one 
• 1244037-16-8 propane-1-sulfonic acid {2,4-difluoro-3-[5-(2-methoxy-pyrimidin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]phenylamide} 
• 1254168-10-9 2-(2-chloro-6-fluorophenyl)-5-(2-methoxypyrimidin-5-yl)-1H-imidazole-4-carbonitrile 
• 1380106-68-2 3-[2-chloro-4-(2-methoxy-pyrimidin-5-yl)-phenyl]-N-hydroxy-acrylamide 
• 1381889-75-3 C₂₀H₂₀N₂O₄ 
• 1420620-46-7 C₃₀H₂₆N₈O₂ 
• 1013101-61-5 C₂₁H₂₅N₇O₄ 
• 1013101-43-3 C₂₁H₂₆N₆O₄ 
• 1013101-37-5 C₂₁H₂₆N₆O₄ 
• 1451274-22-8 5-bromo-2-methoxy-N-[5-(2-methoxypyrimidin-5-yl)pyridin-3-yl]benzenesulfonamide 

Relevant academic research and scientific papers

Flow Chemistry on Multigram Scale: Continuous Synthesis of Boronic Acids within 1 s

The benefits and limitations of a simple continuous flow setup for handling and performing of organolithium chemistry on the multigram scale is described. The developed metalation platform embodies a valuable complement to existing methodologies, as it combines the benefits of Flash Chemistry (chemical synthesis on a time scale of 1 s) with remarkable throughput (g/min) while mitigating the risk of blockages.

Novel bisaryl substituted thiazoles and oxazoles as highly potent and selective peroxisome proliferator-activated receptor δ agonists

The discovery, synthesis, and optimization of compound 1 from a high-throughput screening hit to highly potent and selective peroxisome proliferator-activated receptor δ (PPARδ) agonists are reported. The synthesis and structure-activity relationship in this series are described in detail. On the basis of a general schematic PPAR pharmacophore model, scaffold 1 was divided into headgroup, linker, and tailgroup and successively optimized for PPAR activation using in vitro PPAR transactivation assays. A (2-methylphenoxy)acetic acid headgroup, a flexible linker, and a five-membered heteroaromatic center ring with two hydrophobic aryl substituents were required for efficient and selective PPARδ activation. The fine-tuning of these aryl substituents led to an array of highly potent and selective compounds such as compound 38c, displaying an excellent pharmacokinetic profile in mouse. In an in vivo acute dosing model, selected members of this array were shown to induce the expression of pyruvate dehydrogenase kinase-4 (PDK4) and uncoupling protein-3 (UCP3), genes that are known to be involved in energy homeostasis and regulated by PPARδ in skeletal muscle.

Efficient hydrolysis of organotrifluoroborates via silica gel and water

(Chemical Equation Presented) A general, mild, and efficient method for the hydrolysis of organotrifluoroborates to unveil boronic acids using silica gel and H2O was developed. This method proved to be tolerant of a broad range of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates as well as structurally diverse aminomethylated organotrifluoroborates.As anticipated, electron-rich substrates provided the corresponding boronic acids more readily than electron-poor substrates, owing to the resonance-stabilized difluoroborane intermediate. The method developed was expanded further for the conversion of organotrifluoroborates to the corresponding boronate esters. 2009 American Chemical Society.

5-Pyrimidylboronic acid and 2-methoxy-5-pyrimidylboronic acid: New heteroarylpyrimidine derivatives via Suzuki cross-coupling reactions

5-Pyrimidylboronic acid 2 and 2-methoxy-5-pyrimidylboronic acid 4 have been synthesised by lithium-halogen exchange reactions on 5-bromopyrimidine and 2-methoxy-5-bromopyrimidine, respectively, followed by reaction with triisopropylborate. Suzuki cross-coupling reactions of 2 and 4 with heteroaryl halides [Na2CO3, Pd(PPh3)2Cl 2, 1,4-dioxane, 95°C] yield heteroarylpyrimidines (heteroaryl = thienyl, quinolyl and pyrimidyl). Two-fold reaction of 2 with 4,6-dichloropyrimidine 12 gave 4,6-bis(5-pyrimidyl)pyrimidine 8 (56% yield). Reaction of 4,6-dichloro-pyrimidine with 2-methoxy-5-pyridylboronic acid gave 4,6-bis(2-methoxy-5-pyridyl)pyrimidine 14 (84% yield). Conversion of 14 into 4,6-bis(2-chloro-5-pyridyl)pyrimidine 15 (63% yield) followed by two-fold Suzuki reaction with 4-tert-butylbenzeneboronic acid gave the penta-arylene derivative 4,6-bis(2-(4-ferf-butyl)phenyl-5-pyridyl]pyrimidine 16 (16% yield). Analogous reaction of 12 with 2-methoxy-3-pyridylboronic acid 17 gave 4,6-bis(2-methoxy-3- pyridyl)pyrimidine 18 (64% yield). The X-ray crystal structures of compound 2.05H2O and compound 18 are reported. The two hydroxyl H atoms in 2 have the usual exo-endo orientation. However, unlike most arylboronic acids, molecule 2 does not form a centrosymmetric hydrogen-bonded dimer. In molecule 18, the pyridine rings form dihedral angles of 39.9° and 22.8° with the central pyrimidine ring.