4214-59-9

Usage

Uses

Used in Pharmaceutical Industry:
N-(benzyl)-2-aminopyrimidine is used as a building block or intermediate in the synthesis of various pharmaceutical compounds. Its presence in the molecular structure can influence the biological activity and pharmacokinetic properties of the final drug, making it a valuable component in drug design and development.
Used in Chemical Synthesis:
In the field of organic chemistry, N-(benzyl)-2-aminopyrimidine is used as a versatile reagent and intermediate for the preparation of a wide range of organic compounds. Its ability to participate in various chemical reactions, such as nucleophilic substitution, addition, and condensation, makes it a useful component in the synthesis of complex organic molecules.
Used in Catalyst Preparation:
N-(benzyl)-2-aminopyrimidine is used in the preparation of oxalic acid monoamide ligand compounds for catalysis of coupling reactions. These ligands can enhance the efficiency and selectivity of various coupling reactions, which are crucial in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C11H11N3/c1-2-5-10(6-3-1)9-14-11-12-7-4-8-13-11/h1-8H,9H2,(H,12,13,14)

Upstream product

• 109-12-6 2-aminopyrimidine 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 
• 823-09-6 2-(methylsulfanyl)pyrimidine 
• 100-46-9 benzylamine 
• 18213-90-6 2-phenoxypyrimidine 
• 76175-65-0 N-benzyl-4,6-dichloropyrimidin-2-amine 
• 91093-25-3 N-(benzylidene)-2-aminopyrimidine 
• 624-67-9 Propargylic aldehyde 
• 100-39-0 benzyl bromide 
• 157020-16-1 N-(pyrimidin-2'-yl)pyridinium aminide 
• 108-88-3 toluene 
• 41855-81-6 N,N'-Benzyliden-bis(2-aminopyrimidin) 
• 1722-12-9 2-chloropyrimidine 

Downstream Products

• 531-08-8 RP 2971 
• 38373-55-6 benzyl-(5-bromo-pyrimidin-2-yl)-amine 
• 1042274-94-1 2-(4-chlorophenyl)-2-hydroxy-1-benzyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium bromide 
• 1313613-46-5 Br^(1-)*C₁₉H₁₇IN₃O⁽¹⁺⁾ 
• 1402816-35-6 1-acetyl-3-benzyl-1-tert-butyl-3-pyrimidin-2-yl-urea 
• 946778-44-5 2-(N-benzylamino)pyrimidine-5-carbaldehyde 

Relevant academic research and scientific papers

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalys

Nickel?Copper bimetallic mesoporous nanoparticles: As an efficient heterogeneous catalyst for N-alkylation of amines with alcohols

A bimetallic catalyst (Ni/Cu-MCM-41) is prepared via co-condensation method. The latter is characterized by Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), diffuse reflectance spectroscopy (DRS), and nitrogen adsorption–desorption analysis. Catalytic performance of Ni/Cu-MCM-41 is probed in N-alkylation of amines with alcohols through a hydrogen autotransfer process. Noteworthy, this catalytic system appears very efficient for synthesis of a range of secondary and tertiary amines in good to excellent isolated yields. Moreover, the catalyst is successfully recovered and reused four times without notable decrease in its activity.

Mimicking transition metals in borrowing hydrogen from alcohols

Borrowing hydrogen from alcohols, storing it on a catalyst and subsequent transfer of the hydrogen from the catalyst to anin situgenerated imine is the hallmark of a transition metal mediated catalyticN-alkylation of amines. However, such a borrowing hydrogen mechanism with a transition metal free catalytic system which stores hydrogen molecules in the catalyst backbone is yet to be established. Herein, we demonstrate that a phenalenyl ligand can imitate the role of transition metals in storing and transferring hydrogen molecules leading to borrowing hydrogen mediated alkylation of anilines by alcohols including a wide range of substrate scope. A close inspection of the mechanistic pathway by characterizing several intermediates through various spectroscopic techniques, deuterium labelling experiments, and DFT study concluded that the phenalenyl radical based backbone sequentially adds H+, H˙ and an electron through a dearomatization process which are subsequently used as reducing equivalents to the C-N double bond in a catalytic fashion.

Iron-Catalyzed Oxidative Amination of Benzylic C(sp3)–H Bonds with Anilines

Iron-catalyzed oxidative amination of benzylic C(sp3)–H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) is realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of the iron metal center. Using DTBP as oxidant, [HItBu][FeBr4] showed the highest catalytic activity for anilines bearing EWGs, while [HIPym][FeBr4] was more efficient for EDG-substituted anilines. This work provides alternative access to benzylamines with the advantages of both a wide substrate scope and iron catalysis.

Dialkylterphenyl Phosphine-Based Palladium Precatalysts for Efficient Aryl Amination of N-Nucleophiles

A series of 2-aminobiphenyl palladacycles supported by dialkylterphenyl phosphines, PR2Ar′ (R=Me, Et, iPr, Cyp (cyclopentyl), Ar′=ArDipp2, ArXyl2f, Dipp (2,6-C6H3-(2,6-C6H3-(CHMe2)2)2), Xyl=xylyl) have been prepared and structurally characterized. Neutral palladacycles were obtained with less bulky terphenyl phosphines (i.e., Me and Et substituents) whereas the largest phosphines provided cationic palladacycles in which the phosphines adopted a bidentate hemilabile k1-P,η1-Carene coordination mode. The influence of the ligand structure on the catalytic performance of these Pd precatalysts was evaluated in aryl amination reactions. Cationic complexes bearing the phosphines PiPr2ArXyl2 and PCyp2ArXyl2 were the most active of the series. These precatalysts have demonstrated a high versatility and efficiency in the coupling of a variety of nitrogen nucleophiles, including secondary amines, alkyl amines, anilines, and indoles, with electronically deactivated and ortho-substituted aryl chlorides at low catalyst loadings (0.25–0.75 mol % Pd) and without excess ligand.

Nickel(II)-NΛNΛO Pincer Type Complex-Catalyzed N-alkylation of Amines with Alcohols via the Hydrogen Autotransfer Reaction

A highly sustainable catalytic protocol for the coupling of alcohols and amines for selective monoalkylated amines using Ni(II)-NΛNΛO pincer type complexes through the borrowing hydrogen methodology is described. An array of Ni(II) catalysts (1-3) was synthesized and characterized by various spectral and analytical methods. Furthermore, the distorted square planar geometry of the complexes (1 and 2) was substantiated with single crystal X-ray diffraction study. The inexpensive nickel-based catalytic methodology displays a broad substrate scope for the N-alkylation of aromatic and heteroaromatic amines using a diverse range of primary alcohols with excellent yields up to 97%. The present approach is environmentally benign, which liberates water as the sole byproduct. A short synthesis of drug intermediates such as mepyramine and chloropyramine illustrates the utility of the present protocol.

Bidentate geometry-constrained iminopyridyl nickel-catalyzed synthesis of amines or imines via borrowing hydrogen or dehydrogenative condensation

The efficient Ni-catalyzed N-alkylation of various anilines with alcohols via borrowing hydrogen is reported using a bidentate geometry-constrained iminopyridyl nickel complex as the catalyst. Substituted benzylic alcohols and short/long chain aliphatic alcohols could be applied as the alkylation sources to couple with aromatic and heteroaromatic amines to give a diverse set of N-alkylation outcomes in moderate to excellent yields. The nickel catalytic system was also suitable for aliphatic amines, selectively delivering the corresponding imines via an acceptorless dehydrogenative condensation strategy.

Zinc-Catalyzed N-Alkylation of Aromatic Amines with Alcohols: A Ligand-Free Approach

An efficient zinc-catalyzed N-alkylation reaction of aromatic amines was achieved using aliphatic, aromatic, and heteroaromatic alcohols as the alkylating reagent. A variety of aniline derivatives, including heteroaromatic amines, underwent the N-alkylation reaction and furnished the corresponding monoalkylated products in good to excellent yields. The application of the reaction is also further demonstrated by the synthesis of a 2-phenylquinoline derivative from acetophenone and 2-aminobenzyl alcohol. Deuterium labeling experiments show that the reaction proceeds via a borrowing hydrogen process. (Figure presented.).

Pyridine mediated transition-metal-free direct alkylation of anilines using alcohols: via borrowing hydrogen conditions

Herein, we report pyridine and other similar azaaromatics as efficient biomimetic hydrogen shuttles for a transition-metal-free direct N-alkylation of aryl and heteroaryl amines using a variety of benzylic and straight chain alcohols. Mechanistic studies including deuterium labeling and the isolation of dihydro-intermediates of the benzannulated pyridine confirmed the role of pyridine and a borrowing hydrogen process operating in these reactions. In addition, we have extended this methodology for the development of dehydrogenative synthesis of quinolines and indoles, as well as the transfer hydrogenation of ketones. This journal is

Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides

The present invention provides oxalic amide ligands and uses thereof in copper-catalyzed coupling reaction of aryl halides. Specifically, the present invention provides a use of a compound represented by formula I, wherein definitions of each group are described in the specification. The compound represented by formula I can be used as a ligand in copper-catalyzed coupling reaction of aryl halides for the formation of C—N, C—O and C—S bonds.