402960-38-7

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINOPYRIMIDINE-5-BORONIC ACID, PINACOL ESTER is used as a chemical intermediate for the development of PI3K inhibitors. These inhibitors play a crucial role in the treatment of various cancers by targeting the PI3K pathway, which is often dysregulated in malignant cells, leading to uncontrolled cell growth and survival.
2-AMINOPYRIMIDINE-5-BORONIC ACID, PINACOL ESTER's utility in the pharmaceutical industry lies in its ability to be further modified and incorporated into more complex molecular structures with potential therapeutic applications. Its use in the preparation of PI3K inhibitors highlights its importance in the ongoing research and development of novel cancer treatments.

InChI:InChI:1S/C10H16BN3O2/c1-9(2)10(3,4)16-11(15-9)7-5-13-8(12)14-6-7/h5-6H,1-4H3,(H2,12,13,14)

Upstream product

• 7752-82-1 5-bromo-2-aminopyrimidine 
• 73183-34-3 bis(pinacol)diborane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 121-43-7 Trimethyl borate 
• 1072850-89-5 benzhydrylidene-(5-bromo-pyrimidine-2-yl)amine 
• 1445-39-2 2-amino-5-iodopyrimidine 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 1336-21-6 ammonium hydroxide 
• 1003845-08-6 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine 

Downstream Products

• 1033735-88-4 5-(7-methyl-6-(3-(methylsulfonyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine 
• 1033741-60-4 2-(2-(3-(2-(2-aminopyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenylamino)ethoxy)ethanol 
• 1155305-07-9 6-[3-(4-methanesulfonylpiperazin-1-yImethyl)phenyl]-2-morpholin-4-yl-[4,5']bipyrimidinyl-2'-ylamine 
• 1155305-12-6 [3-(2'-amino-2-morpholin-4-yl-[4,5']bipyrimidinyl-6-yl)phenyl]methanol 
• 1155304-84-9 N-[4-(2'-amino-2-morpholin-4-yl-[4,5']bipyrimidinyl-6-yl)phenyl]methanesulfonamide 
• 1032754-81-6 GNE-477 
• 1033736-15-0 5-(6-(3-(methylsulfonyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine 
• 1033738-78-1 (3-(2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl)(4-methylpiperazin-1-yl)methanone 
• 1033733-75-3 (3-(2-(2-aminopyrimidin-5-yl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)phenyl)(4-methylpiperazin-1-yl)methanone 
• 1246372-44-0 5-[2-(3,4-dimethoxy-phenyl)-6-methyl-jmidazo[2,1-b][1,3,4]thiadiazol-5-yl]-pyrimidin-2-ylamine 
• 1246372-59-7 4-{4-[5-(2-amino-pyrimidin-5-yl)-imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-2-methoxy-phenoxy}-piperidine-1-carboxylic acid tert-butyl ester 
• 1007207-67-1 CH5132799 
• 1111104-89-2 5-(4-(trifluoromethyl)phenyl)pyrimidin-2-amine 
• 1408145-32-3 3-(2-aminopyrimidin-5-yl)-N-(4-(pyrrolidin-1-yl)-trans-cyclohexyl)imidazo[1,2-b]pyridazin-6-amine 

Relevant academic research and scientific papers

Synthesis and biological activity of new 2,4,6-trisubstituted triazines as potential phosphoinositide 3-kinase inhibitors

Twenty-five novel 2,4,6-trisubstituted triazines were synthesized and biologically evaluated. Most of the compounds synthesized showed good antiproliferative activity against HCT-116 and MCF-7. Compounds B18 and B19 showed the best antiproliferative activity. Further study showed B18 and B19 inhibited four phosphoinositide 3-kinase isoforms and mammalian target of rapamycin with good potency. These results demonstrate that 2,4,6-trisubstituted triazines are potentially useful phosphoinositide 3-kinase inhibitors for the development of new anticancer drugs.

Development of an Efficient Synthesis of (2-Aminopyrimidin-5-yl) Boronic Acid

A practical and cost-effective synthesis of (2-aminopyrimidin-5-yl) boronic acid 1b has been developed. Key features of the synthesis include the inexpensive in situ protection of the amine via bis-silylation using TMSCl followed by metal-halogen exchange using n-BuLi and trapping with B(Oi-Pr)3. The water-soluble boronic acid is isolated by a well-designed acid-base sequence providing the target in 80% yield and high purity for the two-step process. The large-scale (15 kg) implementation of a Suzuki-Miyaura borylation to form the pinacol boronic ester is also described.

Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds

Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.

Transition metal complex, polymer, mixture, composition and organic electronic device

The invention discloses a transition metal complex, a polymer, a mixture, a composition and an organic electronic device. The transition metal complex has a structural general formula represented by achemical formula (1), and is simple to synthesize, novel in structure, relatively good in stability, long in service life and good in light emitting performance; the compound represented by the chemical formula (1) is convenient for realizing an efficient, high-brightness and high-stability OLED device, and a relatively good material option is provided for full-color display and illumination application.

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

2-MORPHOLIN-4,6-DISUBSTITUTED PYRIMIDINE DERIVATIVE, AND PREPARATION METHOD AND PHARMACEUTICAL USE THEREOF

Disclosed is a 2-morpholin-4,6-disubstituted pyrimidine derivative as shown in formula (I) below, and a pharmaceutically acceptable salt, solvate, stereoisomer or prodrug thereof, and a pharmaceutical composition thereof and a use thereof, wherein the definition of each group is as shown in the description. The compound has a PI3K kinase inhibition activity, and has a relatively high inhibitive ability and a low cytotoxicity against PIK3CA mutant breast cancer cell strains T47D and MCF-7.

Early Development Scale-Up of a Structurally-Challenging 5-Lipoxygenase Activating Protein (FLAP) Inhibitor

A practical and efficient synthesis of the FLAP inhibitor 1 was developed addressing multiple scale-up and safety concerns posed by the established synthesis and utilized a resolution strategy (replacing supercritical fluid chromatography (SFC) separation) for expedient access to the key structural component of 1: the challenging chiral quaternary center. Also highlighted are in situ IR monitoring, condensation to form the 1,2,4-oxadiazole ring, and an efficient Suzuki-Miyaura coupling.

Synthesis method of 2-aminopyrimidine-5-boronic acid pinacol ester borate

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of 2-aminopyrimidine-5-boronic acid pinacol ester borate. The synthesis method comprises the following steps: carrying out continuous reaction at the temperature of 50 to 125 DEG C for 3 to 8 hours on 2-amino-5-bromopyrimidine and bisdiboron which serve as raw materials in a proper solvent under the action of specific alkaline potassium acetate and 1,1'-dis(diphenylphosphine) ferrocene] palladium dichloride dichloromethane complex serving as a specific catalyst to generate a 2-aminopyrimidine-5-boronic acid pinacol ester borate coarse product, wherein the amount ratio of the 2-amino-5-bromopyrimidine to the bisdiboron is 1 to (0.95 to 2.1), and the amount ratio of the 2-amino-5-bromopyrimidine to the solvent is 1 to (4.0 to 30); carrying out recrystallization to obtain a 2-aminopyrimidine-5-boronic acid pinacol ester borate pure product. According to the synthesis method, the raw material is relatively easy to obtain, and the operation is easy; the specific alkali and the specific catalyst accelerate the reaction progress and shortens the reaction time; the reaction yield is high, and the purity is high.

BENZODIAZEPINES AS BROMODOMAIN INHIBITORS

The present invention provides novel benzodiazepine derivatives of Formula I or pharmaceutically acceptable derivatives, polymorphs, salts or prodrugs thereof. Said compounds have potential as bromodomain (BRD) inhibitors.

Preparation of 2-amino-pyrimidine-5-boronic acid frequency that ester method

A method of preparing 2-aminopyrimidine-5-boronic acid pinacol ester is disclosed. The method includes subjecting 2-chloropyrimidine that is a raw material and NBS to bromization under catalysis of BF3-Et2O to obtain 2-chloro-5-bromopyrimidine; reacting the 2-chloro-5-bromopyrimidine with n-Bu3MgLi at a temperature ranging from -20 DEG C to -10 DEG C; adding methoxyboronic acid pinacol ester or isopropoxyboronic acid pinacol ester; performing boronization to obtain 2-chloropyrimidine-5-boronic acid pinacol ester; adding into ammonia water or a methanol-ammonia solution; and reacting at 80-100 DEG C in a sealed manner to obtain the 2-chloropyrimidine-5-boronic acid pinacol ester. Synthetic process conditions of the method are mild. An ultralow-temperature reaction is avoided. Reactions can be performed continuously. A pure product can be obtained only by simple recrystallization of the final product.