2305-87-5

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Phenylpyrimidin-2-amine is used as a key intermediate in the synthesis of various pharmaceuticals and biologically active molecules. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Medicinal Chemistry Research:
4-Phenylpyrimidin-2-amine is utilized in medicinal chemistry research to explore its potential role in the treatment of certain diseases and medical conditions. Its chemical properties and reactivity make it a valuable compound for designing and optimizing new therapeutic agents.
Used in Organic Synthesis:
4-Phenylpyrimidin-2-amine is employed in organic synthesis for the preparation of various organic compounds. Its versatility and reactivity contribute to the development of new chemical entities with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H9N3/c11-10-12-7-6-9(13-10)8-4-2-1-3-5-8/h1-7H,(H2,11,12,13)

Upstream product

• 109-12-6 2-aminopyrimidine 
• 591-51-5 phenyllithium 
• 506-93-4 guanidine nitrate 
• 3623-15-2 phenyl propargyl ketone 
• 64-17-5 ethanol 
• 50-01-1 guanidine hydrochloride 
• 15397-33-8 3-Oxo-3-phenylpropanal 
• 3438-48-0 4-phenylpyrimidine 
• 91093-42-4 2-amino-4-phenylpyrimidine-5-carboxylic acid 
• 4452-12-4 1-phenyl-3-(piperidin-1-yl)prop-2-en-1-one 
• 4623-58-9 3-phenoxy-1-phenyl-propenone 
• 545-06-2 trichloroacetonitrile 
• 14161-40-1 4-phenylpyrimidine-1-oxide 
• 77995-05-2 2-amino-4-phenyl-pyrimidine-5-carboxylic acid ethyl ester 

Downstream Products

• 38675-31-9 4-phenyl-1H-pyrimidin-2-one 
• 80830-66-6 2-Benzylamino-4-phenylpyrimidine 
• 13036-50-5 2-chloro-4-phenylpyrimidine 
• 38675-31-9 2-hydroxy-4-phenylpyrimidine 
• 85658-55-5 5-bromo-2-amino-4-phenylpyrimidine 
• 80830-43-9 2-Amino-4-phenylpyrimidine 1-Oxide 
• 101117-39-9 N,4-diphenylpyrimidin-2-amine 
• 1205602-97-6 (S)-2-(4-Phenyl-pyrimidin-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1300056-87-4 1-[1-(3-dimethylaminopropyl)-1H-indol-3-yl]-3-(4-phenyl-pyrimidin-2-yl)urea 
• 782450-12-8 6-methyl-N-(4-phenylpyrimidin-2-yl)benzene-1,3-diamine 
• 1346617-92-2 N-(5-azido-2-methylphenyl)-4-phenylpyrimidin-2-amine 
• 1346617-87-5 N-[2-methyl-5-(4-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}-1H-1,2,3-triazol-1-yl)phenyl]-4-phenylpyrimidin-2-amine 
• 1346617-88-6 methyl 1-[4-methyl-3-(4-phenylpyrimidin-2-ylamino)phenyl]-1H-1,2,3-triazole-4-carboxylate 
• 1346617-89-7 N-[2-methyl-5-{4-[(dimethylamino)methyl]-1H-1,2,3-triazol-1-yl}-phenyl]-4-phenylpyrimidin-2-amine 

Relevant academic research and scientific papers

Synthesis of 2-Amino-5-acylthiazoles by a Tertiary Amine-Promoted One-Pot Three-Component Cascade Cyclization Using Elemental Sulfur as a Sulfur Source

A novel one-pot three-component cascade cyclization strategy for the synthesis of 2-amino-5-acylthiazoles using enaminones, cyanamide, and elemental sulfur has been developed. The reported methods have demonstrated good tolerance of various functional gro

Nucleophilic substitution or dipolar 1,3-cycloaddition in reactions of cyanamide with 4-arylpyrimidine 1-oxides

Pyrimidine 1-oxides with cyanamide afforded 2-ureidopyrimidines as the result of the nucleophilic substitution of hydrogen, whereas the formation of similar 2-trichloroacetylaminopyrimidines occurs as dipolar 1,3-cycloaddition of the same oxides to trichl

Gold(i) complexes with heteroaryl phosphine ligands

Gold(i) complexes ligated by phosphines with N-heterocycles in the periphery were prepared. First the synthesis of the ligands N- (diphenylphosphino)-4-(pyridin-2-yl)pyrimidin-2-amine (Hpypya) and N-(diphenylphosphino)-4-phenylpyrimidin-2-amine (Hphpya) a

C2-Selective, Functional-Group-Divergent Amination of Pyrimidines by Enthalpy-Controlled Nucleophilic Functionalization

Synthesis of heteroaryl amines has been an important topic in organic chemistry because of their importance in small-molecule discovery. In particular, 2-Aminopyrimidines represent a highly privileged structural motif that is prevalent in bioactive molecules, but a general strategy to introduce the pyrimidine C2-N bonds via direct functionalization is elusive. Here we describe a synthetic platform for site-selective C-H functionalization that affords pyrimidinyl iminium salt intermediates, which then can be transformed into various amine products in situ. Mechanism-based reagent design allowed for the C2-selective amination of pyrimidines, opening the new scope of site-selective heteroaryl C-H functionalization. Our method is compatible with a broad range of pyrimidines with sensitive functional groups and can access complex aminopyrimidines with high selectivity.

I2-Catalyzed Aerobic α,β-Dehydrogenation and Deamination of Tertiary Alkylamines: Highly Selective Synthesis of Polysubstituted Pyrimidines via Hidden Acyclic Enamines

A novel and efficient entrance to the pyrimidine skeleton has been presented via the α,β-dehydrogenation and deamination of tertiary alkylamines. This I2-catalyzed dehydrogenative multicomponent procedure utilizes simple aldehydes to trap the hidden enami

Discovery of coumarin derivatives as potent and selective cyclin-dependent kinase 9 (CDK9) inhibitors with high antitumour activity

Specific inhibition of CDK9 is considered a promising strategy for developing effective anticancer therapeutics. However, most of the reported CDK9 inhibitors are still at an early stage of development and lack selectivity against other CDKs. Herein, we discovered coumarin derivative 30i as a potent CDK9 inhibitor with high selectivity (8300-fold over CDK7). Binding mode analysis illustrated that the substituent coumarin moiety is a critical group for CDK9 selectivity by occupying a flexible hinge/αD region, which is sterically hindered in other CDKs. Compound 30i showed excellent cellular antiproliferative activity, moderate pharmacokinetic property and low hERG inhibition. Moreover, 30i significantly induced tumour growth inhibition in a dose-dependent manner without causing an obvious loss of body weight in an MV4-11 xenograft mice model. Altogether, these results suggest that 30i may serve as a potential acute myeloid leukaemia (AML) therapeutics by selectively targeting CDK9.

Synthesis of C5-tethered indolyl-3-glyoxylamide derivatives as tubulin polymerization inhibitors

A series of C5-tethered Indolyl-3-glyoxylamide derivatives were synthesized and evaluated for their in?vitro cytotoxic activity against DU145 (prostate), PC-3 (prostate), A549 (lung) and HCT-15 (colon) cancer cell lines by employing the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized compounds, compound 7f displayed cytotoxicity of IC50?=?140?nM towards DU145 cancer cell line. The treatment of DU145?cells with 7f led to inhibition of cell migration ability. Futher, the detailed studies such as acridine orange/ethidium Bromide (AO/EB), DAPI, annexin V-FITC/propidium iodide staining assay suggested that the compound 7f induced apoptosis in DU145?cells. The influence of the cytotoxic compound 7f on the cell cycle distribution was assessed on the DU145?cell line, exhibiting a cell cycle arrest at the G2/M phase (hallmark of tubulin polymerization) and next inhibited tubulin polymerization with IC500.40?μM. Furthermore, the treatment with compound 7f caused collapse of mitochondrial membrane potential and elevated intracellular superoxide ROS levels in DU145?cells. Western blotting was performed to examine the levels of apoptotic proteins (Bcl-2 and Bax); the study confirmed that compound 7f induced apoptosis through apoptosis-related protein expression. Thus, these studies provided a new molecular scaffold for the further development of anticancer agents that target tubulin.

Transition Metal Free Intermolecular Direct Oxidative C-N Bond Formation to Polysubstituted Pyrimidines Using Molecular Oxygen as the Sole Oxidant

Various polysubstituted pyrimidines are smoothly formed via a base-promoted intermolecular oxidation C-N bond formation of allylic C(sp3)-H and vinylic C(sp2)-H of allyllic compounds with amidines using O2 as the sole oxid

Synthesis and biological evaluation of oxindole linked indolyl-pyrimidine derivatives as potential cytotoxic agents

In our endeavor towards the development of effective cytotoxic agents, a series of oxindole linked indolyl-pyrimidine derivatives were synthesized and characterized by IR, 1H NMR, 13C NMR and Mass spectral analysis. All the newly synthesized target compounds were assessed against PA-1 (ovarian), U-87MG (glioblastoma), LnCaP (prostate), and MCF-7 (Breast) cancer cell lines for their cytotoxic potential, with majority of them showing inhibitory activity at low micro-molar concentrations. Significantly, compound 8e was found to be most potent amongst all the tested compounds with an IC50 value of (2.43 ± 0.29 μM) on PA-1 cells. The influence of the most active cytotoxic compound 8e on the cell cycle distribution was assessed on the PA-1 cell line, exhibiting a cell cycle arrest at the G2/M phase. Moreover, acridine orange/ethidium bromide staining and annexin V binding assay confirmed that compound 8e can induce cell apoptosis in PA-1 cells. These preliminary results persuade further investigation on the synthesized compounds aiming to the development of potential cytotoxic agents.

Base mediated direct C-H amination for pyrimidines synthesis from amidines and cinnamaldehydes using oxygen as green oxidants

A direct metal-free C-H amination reaction of cinnamaldehydes and amidines to realize the synthesis of polysubstituted pyrimidines was developed in the presence of base. This greener synthetic methodology provides a straightforward approach to the synthes