Production Method 1

942947-94-6

73183-34-3

944401-60-9

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  overnight, 115 °C; 115 °C → rt
1.2 Reagents: Water Solvents: Ethyl acetate

Reference

Preparation of 2-Morpholino-4,6-disubstituted pyrimidine analogues and their application as anticancer agents

, World Intellectual Property Organization, , ,

Production Method 2

942947-94-6

73183-34-3

944401-60-9

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  overnight, 115 °C

Reference

Preparation of PI3K inhibitor, pharmaceutically acceptable salts, polycrystalline forms, and application thereof

, World Intellectual Property Organization, , ,

Production Method 3

942947-94-6

73183-34-3

944401-60-9

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  6 h, 115 °C

Reference

Preparation of dimorpholinopyrimidines for inhibiting hamartoma tumor cells

, World Intellectual Property Organization, , ,

Production Method 4

942947-94-6

73183-34-3

944401-60-9

Reaction Conditions

1.1 Reagents: Potassium acetate Solvents: 1,4-Dioxane ;  15 min, rt
1.2 Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… ;  6 h, 115 °C; 115 °C → rt

Reference

Pyrimidine derivatives used as PI-3 kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 5

944401-60-9

Reaction Conditions

Reference

Preparation of substituted pyridines as Tyk-2 inhibitors

, World Intellectual Property Organization, , ,

Production Method 6

944401-60-9

Reaction Conditions

Reference

Method of inhibiting hamartoma tumor cells

, United States, , ,

Production Method 7

942947-94-6

73183-34-3

944401-60-9

19798-80-2

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  6 h, 115 °C

Reference

Identification of NVP-BKM120 as a Potent, Selective, Orally Bioavailable Class I PI3 Kinase Inhibitor for Treating Cancer

Burger, Matthew T.; Pecchi, Sabina; Wagman, Allan; Ni, Zhi-Jie; Knapp, Mark; et al, ACS Medicinal Chemistry Letters, 2011, 2(10), 774-779

4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine Raw materials

• 5-Bromo-4-chloropyridin-2-amine
• Bis(pinacolato)diborane

4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine Preparation Products

• 4-Chloro-pyridin-2-ylamine (19798-80-2)
• 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (944401-60-9)

• 1. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 2. Empowering microfluidics by micro-3D printing and solution-based mineral coating?
  Hongxia Li,Aikifa Raza,Qiaoyu Ge,Jin-You Lu,TieJun Zhang Soft Matter, 2020,16, 6841-6849
• 3. Fast-pulsing NMR techniques for the detection of weak interactions: successful natural abundance probe of hydrogen bonds in peptides?
  Amandine Altmayer-Henzien,Valérie Declerck,David J. Aitken,Ewen Lescop,Denis Merlet,Jonathan Farjon Org. Biomol. Chem., 2013,11, 7611-7615
• 4. Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials?
  Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-Garayoa RSC Adv., 2017,7, 24133-24139
• 5. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
  Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong Wu J. Mater. Chem. A, 2019,7, 17995-18002

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Aminopyridines and derivatives

4-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine: A Versatile Building Block in Medicinal Chemistry

4-Chloro-5-(4,4,5,5-tetamethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (CAS No. 944401-60-9) is a highly versatile compound that has gained significant attention in the field of medicinal chemistry and drug discovery. This compound is a key intermediate in the synthesis of various bioactive molecules and pharmaceuticals. Its unique structural features and reactivity make it an essential tool for researchers and chemists working on the development of novel therapeutic agents.

The chemical structure of 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine consists of a pyridine ring substituted with a chloro group at the 4-position and a boronic ester moiety at the 5-position. The boronic ester functionality is particularly important as it allows for efficient and selective coupling reactions via Suzuki-Miyaura cross-coupling. This reaction is widely used in the synthesis of complex organic molecules and has been instrumental in the development of numerous drugs and drug candidates.

Recent research advancements have highlighted the potential of 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine in various therapeutic areas. For instance, studies have shown that this compound can be used to synthesize potent inhibitors of kinases, which are key targets in cancer therapy. One notable example is the synthesis of a series of pyridine-based inhibitors that exhibit high selectivity and efficacy against specific kinases involved in tumor growth and metastasis.

In addition to its applications in cancer research, 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine has also been explored for its potential in the treatment of neurodegenerative diseases. Researchers have utilized this compound to develop small molecules that can modulate specific protein-protein interactions involved in conditions such as Alzheimer's disease and Parkinson's disease. These molecules have shown promising results in preclinical studies and are currently being evaluated for their therapeutic potential.

The synthetic versatility of 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine is further enhanced by its ability to undergo a wide range of chemical transformations. For example, the chloro group can be readily replaced with other functional groups through nucleophilic substitution reactions. This flexibility allows chemists to tailor the properties of the final product to meet specific biological or pharmacological requirements.

Moreover, the stability and solubility properties of 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine make it an ideal starting material for high-throughput screening (HTS) campaigns. HTS is a critical step in drug discovery that involves testing large libraries of compounds for their biological activity. The ease with which this compound can be synthesized and purified ensures that it can be readily incorporated into HTS workflows without compromising efficiency or accuracy.

The environmental impact of using 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine in chemical processes has also been a focus of recent studies. Researchers have developed greener synthetic methods that minimize waste generation and reduce the use of hazardous reagents. These sustainable approaches not only align with environmental regulations but also contribute to the overall cost-effectiveness and scalability of drug production processes.

In conclusion, 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-y^l)pyridin^-2^-amine (CAS No. 944401^-60^-9) is a valuable building block in medicinal chemistry due to its unique structural features and reactivity. Its applications span multiple therapeutic areas and its synthetic versatility makes it an indispensable tool for researchers and chemists working on the development of novel drugs and bioactive molecules. As research continues to advance in this field, it is likely that new applications for this compound will be discovered, further solidifying its importance in modern medicinal chemistry.

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