936250-22-5

Basic information

• Product Name: 2-Amino-pyrimidine-5-boronic acid
• Synonyms: 2-Aminopyrimidine-5-boronic acid;2-Aminopyrimidine-5-ylboronic acid;2-aminopyrimidin-5-yl-5-boronic acid;2-Aminopyrimidine-5-boron...;2-AMinopyriMidine-5-boronic;2-Amino-5-boronopyrimidine;2-AMino-5-pyriMidineboronic acid;2-aMino-4-pyMidine boronic acid
• CAS NO: 936250-22-5
• Molecular Formula: C₄H₆BN₃O₂
• Molecular Weight: 138.92
• Product Categories: Organic boronic acid
• Mol File: 936250-22-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 206-211℃
• Boiling Point: 486.995 °C at 760 mmHg
• Flash Point: 248.326 °C
• Appearance: /Solid
• Density: 1.443 g/cm³
• Vapor Pressure: 2.68E-10mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 2.58±0.11(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-Amino-pyrimidine-5-boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-pyrimidine-5-boronic acid(936250-22-5)
• EPA Substance Registry System: 2-Amino-pyrimidine-5-boronic acid(936250-22-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 2
• Hazardous Substances Data: 936250-22-5(Hazardous Substances Data)

Usage

Uses

2-Aminopyrimidine-5-boronic acid is used as pharmaceutical intermediates.

InChI:InChI=1/C4H6BN3O2/c6-4-7-1-3(2-8-4)5(9)10/h1-2,9-10H,(H2,6,7,8)

Upstream product

• 5419-55-6 Triisopropyl borate 
• 883231-25-2 (2-((tert-butoxycarbonyl)amino)pyrimidin-5-yl)boronic acid 
• 7752-82-1 5-bromo-2-aminopyrimidine 
• 402960-38-7 5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyrimidin-2-ylamine 

Downstream Products

• 197958-23-9 2-amino-5-(pyridin-3-yl)pyrimidine 
• 13481-05-5 2-amino-5-pyrazinylpyrimidine 
• 1004972-21-7 2-amino-5-benzothiazol-2-ylpyrimidine 
• 31402-65-0 4-(2-aminopyrimidin-5-yl)nitrobenzene 
• 1004972-16-0 3-(2-aminopyrimidin-5-yl)quinoline 
• 1004972-23-9 3-bromo-6-(2-aminopyrimidin-5-yl)pyridine 
• 1062204-37-8 5-[9-(1-benzylpiperidin-4-yl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine 
• 1155304-82-7 2-morpholin-4-yl-6-phenoxy-[4,5']bipyrimidinyl-2'-ylamine 
• 1241826-62-9 N-(4-(2-aminopyrimidin-5-yl)-2-(trifluoromethoxy)benzyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide 
• 1241826-72-1 N-(4-(2-aminopyrimidin-5-yl)-2-(trifluoromethoxy)benzyl)-2-(2-cyanoethyl)-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide 
• 31408-23-8 5-phenyl-pyrimidin-2-ylamine 
• 1252598-10-9 C₁₂H₁₅N₇O 
• 1557079-84-1 1-(4-((2-(2-aminopyrimidin-5-yl)-4-morpholinopyrido[3,2-d]pyrimidin-7-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one 
• 1557079-59-0 5-(7-(3-(methylsulfonyl)phenyl)-4-morpholinoquinazolin-2-yl)pyrimidin-2-amine 

Relevant articles and documents

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.

PROCESS FOR THE PREPARATION OF BORONIC ACID INTERMEDIATES

The present invention relates to an improved process for the preparation of 2- pyrimidine-5-boronic acid of formula (I). or salts or esters thereof.

Identification of NVP-BKM120 as a potent, selective, orally bioavailable class i PI3 kinase inhibitor for treating cancer

Phosphoinositide-3-kinases (PI3Ks) are important oncology targets due to the deregulation of this signaling pathway in a wide variety of human cancers. Herein we describe the structure guided optimization of a series of 2-morpholino, 4-substituted, 6-heterocyclic pyrimidines where the pharmacokinetic properties were improved by modulating the electronics of the 6-position heterocycle, and the overall druglike properties were fine-tuned further by modification of the 4-position substituent. The resulting 2,4-bismorpholino 6-heterocyclic pyrimidines are potent class I PI3K inhibitors showing mechanism modulation in PI3K dependent cell lines and in vivo efficacy in tumor xenograft models with PI3K pathway deregulation (A2780 ovarian and U87MG glioma). These efforts culminated in the discovery of 15 (NVP-BKM120), currently in Phase II clinical trials for the treatment of cancer.