6957-21-7

Usage

Uses

Used in Pharmaceutical Industry:
N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine is used as a reagent for the preparation of 2-(Benzylidineamino)pyrimidines, which are antihistaminic agents. These agents are crucial in the development of medications aimed at treating allergic reactions and conditions such as hay fever, hives, and other histamine-mediated responses.
In the synthesis of these antihistamines, N-[(4-methoxyphenyl)methyl]pyrimidin-2-amine serves as a key intermediate, providing a platform for the attachment of various substituents that can modulate the pharmacological properties of the final drug product. This allows for the fine-tuning of drug efficacy, selectivity, and safety profiles, ultimately leading to the creation of more effective and targeted therapeutics for patients suffering from allergic conditions.

InChI:InChI=1/C12H13N3O/c1-16-11-5-3-10(4-6-11)9-15-12-13-7-2-8-14-12/h2-8H,9H2,1H3,(H,13,14,15)

Upstream product

• 109-12-6 2-aminopyrimidine 
• 123-11-5 4-methoxy-benzaldehyde 
• 824-94-2 p-methoxybenzyl chloride 
• 1722-12-9 2-chloropyrimidine 
• 2393-23-9 4-methoxy-benzylamine 
• 823-09-6 2-(methylsulfanyl)pyrimidine 
• 624-67-9 Propargylic aldehyde 
• 21244-39-3 1-(4-methoxybenzyl)guanidine hemisulfate 
• 41855-81-6 N,N'-Benzyliden-bis(2-aminopyrimidin) 
• 105-13-5 4-Methoxybenzyl alcohol 
• 90042-89-0 4,6-dicloro-2-p.metossibenzilaminopirimidina 
• 4595-60-2 2-bromopyrimidine 
• 45821-44-1 4-methoxy-benzylideneamine 

Downstream Products

• 91-85-0 thonzylamine 
• 109-12-6 2-aminopyrimidine 
• 726-18-1 4,4'-dianisylmethane 
• 104798-89-2 4-(pyrimidin-2ylaminomethyl)phenol 
• 1313613-56-7 Br^(1-)*C₂₀H₁₉BrN₃O₂⁽¹⁺⁾ 

Relevant academic research and scientific papers

CYCLOPROPYL DIHYDROQUINOLINE SULFONAMIDE COMPOUNDS

The present invention provides a compound of Formula (I): an enantiomer, diastereoisomer, atropisomer thereof, a mixture thereof, or a pharmaceutically acceptable salt thereof, that inhibits voltage-gated sodium channels, in particular NaV1.7. The compoun

CYCLOBUTYL DIHYDROQUINOLINE SULFONAMIDE COMPOUNDS

The present invention provides a cyclobutyl dihydroquinoline sulfonamide compound of Formula (I), an enantiomer, diastereoisomer, atropisomer thereof, a mixture thereof, or a pharmaceutically acceptable salt thereof, that inhibits voltage-gated sodium channels, in particular Nav1.7. The compounds are useful for the treatment of diseases associated with the activity of sodium channels such as pain disorders, cough, and itch. Also provided are pharmaceutical compositions containing the compounds of the present invention. Also further provided is an atropi-selective preparation of said compounds of Formula (I), and intermediate thereof.

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.

Transition-Metal-Free Cross-Coupling Reactions in Dynamic Thin Films To Access Pyrimidine and Quinoxaline Analogues

The vortex fluidic device (VFD) is effective in modulating the synthesis of pyrimidine and quinoxaline-based compounds at room temperature and in high yield. The formation of the C–N bond occurs in the absence of a transition-metal catalyst, which avoids the contamination of the products with trace amounts of a transition metal. The systematic investigation of the operating parameters for the microfluidic platform in the confined operation mode established an optimum tilt angle of 45° for a 10 mm diameter borosilicate glass tube rotating at 5000 rpm.

Bicyclic sulfonamide compounds as sodium channel inhibitors

The present invention provides compounds of Formula I, and pharmaceutically acceptable salts thereof, that are inhibitors of voltage-gated sodium channels, in particular Nav1.7. The compounds are useful for the treatment of diseases associated with the activity of sodium channels such as pain disorders and itch. Also provided are pharmaceutical compositions containing compounds of the present invention.

Ruthenium(II) complexes containing a phosphine-functionalized thiosemicarbazone ligand: Synthesis, structures and catalytic C-N bond formation reactions via N-alkylation

A series of ruthenium(II) complexes incorporating a thiosemicarbazone chelate tethered with a diphenylphosphine pendant have been studied. Thus, [(PNS-Et)RuCl(CO)(PPh3)] (1), [N,S-(PNS-Et)RuH(CO)(PPh3)2] (2) and [(PNS-Et)RuCl(PPh3)] (3) were synthesized by reactions of various RuII precursors with 2-(2-(diphenylphosphino)benzylidene)-N-ethylthiosemicarbazone (PNS-Et). However, complexation of PNS-Et with an equimolar amount of [RuCl2(dmso)4] resulted in two different entities [(PNS-Et)RuCl(dmso)2] (4) and [(PNS-Et)2Ru] (5) with different structural features in a single reaction. All the RuII complexes have been characterized by analytical and various spectroscopic techniques. Compounds 1-5 were recrystallized, and the X-ray crystal structures have been reported for 1, 2 and 5. In the complexes 1 and 3-5 the ligand coordinated in a tridentate monobasic fashion by forming PNS five- and six-membered rings, whereas in 2, the ligand coordinated in a bidentate monobasic fashion by forming a strained NS four-membered ring. Furthermore, compounds 1-5 showed catalytic activity in N-alkylation of heteroaromatic amines. Notably, complexes 1-3 were found to be very efficient catalysts toward N-alkylation of a wide range of heterocyclic amines with alcohols. In the presence of a catalytic amount of 2 with 50 mol% of KOH, N1,C5-dialkylation of 4-phenylthiazol-2-amine has been investigated. Reaction of in situ generated aldehyde with amine yields the N1,C5-dialkylated products through the hydride ion transformation from alcohol. Complexes 1-3 also catalyzed a variety of coupling reactions of benzyl alcohols and sulfonamides, which were realized often with 99% isolated yields. Advantageously, only one equivalent of the primary alcohol was consumed in the process.

Structure-dependent tautomerization induced catalyst-free autocatalyzed N-alkylation of heteroaryl amines with alcohols

Catalyst-free autocatalyzed dehydrative N-alkylation reactions of 2-aminobenzothiazoles, 2-aminopyrimidines, and 2-aminopyrazine with primary and secondary alcohols have been achieved for efficient, practical, and green synthesis of the versatile heteroaryl amine derivatives. These reactions were interestingly induced by structure-dependent tautomeric equilibria of the heteroaryl amines via MPV-O transfer hydrogenation of the imino tautomers by alcohols to give aldehydes as the key initiating step.

Efficient and versatile catalysis of N-alkylation of heterocyclic amines with alcohols and one-pot synthesis of 2-aryl substituted benzazoles with newly designed ruthenium(ii) complexes of PNS thiosemicarbazones

Ruthenium(ii) carbonyl complexes with phosphine-functionalized PNS type thiosemicarbazone ligands [RuCl(CO)(EPh3)(L)] (1-6) (E = P or As, L = 2-(2-(diphenylphosphino)benzylidene) thiosemicarbazone (PNS-H), 2-(2-(diphenylphosphino)benzylidene)-N-methylthiosemicarbazone (PNS-Me), 2-(2-(diphenylphosphino)benzylidene)-N-phenylthiosemicarbazone (PNS-Ph)) have been synthesized and characterized by elemental analysis and spectroscopy (IR, UV-Vis, 1H, 13C, 31P-NMR) as well as ESI mass spectrometry. The molecular structures of complexes 1, 2 and 6 were identified by means of single-crystal X-ray diffraction analysis. The analysis revealed that all the complexes possess a distorted octahedral geometry with the ligand coordinating in a uni-negative tridentate PNS fashion. All the ruthenium complexes (1-6) were tested as catalyst for N-alkylation of heteroaromatic amines with alcohols. Notably, complex 2 was found to be a very efficient and versatile catalyst towards N-alkylation of a wide range of heterocyclic amines with alcohols. Complex 2 can also catalyze the direct amination of 2-nitropyridine with benzyl alcohol to the corresponding secondary amine. Furthermore, a preliminary examination of performance for N,N-dialkylation of diamine showed promising results, giving good conversion and high selectivity. In addition, N-alkylation of ortho-substituted anilines (-NH2, -OH and -SH) led to the one-pot synthesis of 2-aryl substituted benzimidazoles, benzoxazoles and benzothiazoles, also revealing the catalytic activity of complex 2. This journal is the Partner Organisations 2014.

Amination of heteroaryl chlorides: Palladium catalysis or SNAr in green solvents?

The reaction of heteroaryl chlorides in the pyrimidine, pyrazine and quinazoline series with amines in water in the presence of KF results in a facile SNAr reaction and N-arylation. The reaction is less satisfactory with pyridines unless an add

Manganese dioxide catalyzed N-alkylation of sulfonamides and amines with alcohols under air

By simply running the reactions under air and solvent-free conditions using catalytic amounts of manganese dioxide, a practical and efficient N-alkylation method for a variety of sulfonamides and amines using alcohols as green alkylating reagents was developed.