152460-09-8

Basic information

• Product Name: N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine
• Synonyms: N-(2-METHYL-5-NITROPHENYL)-4-(PYRIDIN-3-YL)PYRIMIDIN-2-AMINE;2-primidinamine,N-(2-methyl-5-nitrophenyl)-4-(3-pyridinyl);2-pyrimidinamine,N-(2-methyl-5-nitrophenyl)-4-(3-pyridinyl);N-(2-methyl-5-nitrophenyl)-4-(3-pyridinyl)-2-pydimidineamine;(2-methyl-5-nitrophenyl)-(4-(pyridin-3-yl)pyrimidin-2-yl)amine;N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyriMid;2-Methyl-5-nitro-N-[4-(pyridin-3-yl)pyriMidin-2-yl]benzenaMine;IMatinib Related CoMpound
• CAS NO: 152460-09-8
• Molecular Formula: C₁₆H₁₃N₅O₂
• Molecular Weight: 307.31
• EINECS: 1806241-263-5
• Product Categories: Imatinib;Aromatics;Bases & Related Reagents;Nucleotides;Intermediate of Imatinib
• Mol File: 152460-09-8.mol

Chemical Properties

• Melting Point: 188-193°C
• Boiling Point: 546.609 °C at 760 mmHg
• Flash Point: 284.379 °C
• Appearance: Yellow/Solid
• Density: 1.344 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.68±0.12(Predicted)
• CAS DataBase Reference: N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine(152460-09-8)
• EPA Substance Registry System: N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine(152460-09-8)

Safety Data

• Hazardous Substances Data: 152460-09-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine is used as a synthetic building block for the creation of various complex organic molecules. Its application in this field is due to its ability to participate in a range of chemical reactions, such as condensation, substitution, and addition reactions, which are crucial for the synthesis of target compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine is used as a key intermediate in the development of new drugs. Its unique chemical structure allows it to be a potential candidate for the design and synthesis of novel therapeutic agents, particularly those targeting specific biological receptors or enzymes.
Used in Chemical Research:
N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine is also employed in chemical research as a model compound to study various reaction mechanisms and to understand the reactivity of different functional groups. This knowledge can be applied to develop new synthetic strategies and improve existing ones.
Used in Material Science:
In the field of material science, N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine can be used as a component in the development of new materials with specific properties, such as optical, electronic, or magnetic characteristics. Its incorporation into these materials can lead to the creation of advanced materials with potential applications in various industries.

Upstream product

• 55314-16-4 (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 152460-08-7 1-(2-methyl-5-nitrophenyl)guanidine nitrate 
• 55314-16-4 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 350-03-8 methyl-3-pyridylketone 
• 99-55-8 2-methyl-5-nitroaniline 
• 483324-01-2 2-chloro-4-(pyridin-3-yl)pyrimidine 
• 7745-93-9 2-bromo-4-nitrotoluene 
• 66521-66-2 4-pyridin-3-ylpyrimidin-2-ylamine 
• 39883-42-6 β-oxo-3-pyridinepropanal sodium salt 
• 152460-07-6 1-(2-methyl-5-nitrophenyl)guanidine 
• 1026747-41-0 2-[(2-methyl-5-nitrophenyl)amino]-4-(3-pyridinyl)pyrimidine-5-carboxylic acid 
• 152460-08-7 (2-methyl-5-nitrophenyl)guanidine nitrate 
• 1207534-99-3 N-(2-methyl-5-nitrophenyl)guanidinium hydrochloride 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 152459-95-5 imatinib 
• 404844-11-7 4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide 
• 152460-10-1 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine 
• 220127-57-1 imatinib mesylate 
• 475587-16-7 4-chloro-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)benzenesulfonamide 
• 1349893-81-7 N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)biphenyl-4-sulfonamide 
• 1349893-82-8 N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)naphthalene-2-sulfonamide 
• 1349893-83-9 N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)quinoline-3-sulfonamide 
• 1346617-86-4 N-[2-methyl-5-(4-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}-1H-1,2,3-triazol-1-yl)phenyl]-4-(pyridine-3-yl)pyrimidin-2-amine 
• 1450754-50-3 C₂₀H₁₉N₅O₃ 
• 1450754-51-4 C₂₇H₂₈N₈O₂ 
• 593281-60-8 N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-4-(piperidin-1-ylmethyl)benzamide 
• 404843-98-7 N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)-4-(morpholinomethyl)benzamide 
• 809279-56-9 4-((1H-imidazol-1-yl)methyl)-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)benzamide 

Relevant articles and documents

SUBSTITUTED ARYLUREA COMPOUNDS FOR INDUCING APOPTOSIS AND COMPOSITION FOR ANTICANCER COMPRISING THE SAME

The present invention relates to a substituted arylurea compound inducing apoptosis and an anticancer composition comprising the same. The present invention relates to a novel compound capable of preventing, treating and alleviating cancer diseases such as prostate cancer, breast cancer, lung cancer, colorectal cancer, and skin cancer by inhibiting apoptosis of cancer cells and inhibiting proliferation of cancer cells.

Synthesis method of imatinib and imatinib mesylate

The invention relates to a synthesis method of imatinib and imatinib mesylate. The method comprises the following steps: condensing 3-acetylpyridine and N,N-dimethylformamide dimethyl acetal which aretaken as initial raw materials to obtain 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one, then reacting with 2-methyl-5-nitrophenylguanidine nitrate to form a pyrimidine ring, performing nitro reductionto obtain N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidinamine, amidating the N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidinamine and 4-(chloromethyl)benzoyl chloride, performing affinitysubstitution with 1-methylpiperazine to obtain imatinib, and salifying the imatinib and methanesulfonic acid. The products obtained by the method have the advantages of few impurities, simplicity in post-treatment, high total yield, greenness, environmental protection and safety, and is suitable for a production process for large-scale industrial production of imatinib mesylate.

Synthetic method of N-(2-methyl-5-aminophenyl)-4-(3-pyridyl)-2-pyrimidinamine

The invention discloses a synthetic method of N-(2-methyl-5-aminophenyl)-4-(3-pyridyl)-2-pyrimidinamine. The synthetic method comprises the following steps: (1) synthesizing 2-(methylthio)-4-(3-pyridyl) pyrimidine; (2) synthesizing 2-(methylsulfonyl)-4-(3-pyridine) pyrimidine; (3) synthesizing N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidinamine and (4) synthesizing the N-(2-methyl-5-aminophenyl)-4-(3-pyridyl)-2-pyrimidinamine. Synthesis raw materials used in the method are low in price and easy to obtain, reaction conditions are mild, the product yield and purity are high, and the methodis suitable for industrial production. Therefore, the synthetic method disclosed by the invention has good advantages in the aspects of production cost control, environmental friendliness and productquality improvement.

Molecular requirements for the expression of antiplatelet effects by synthetic structural optimized analogues of the anticancer drugs imatinib and nilotinib

Background: Platelets play important roles in cancer progression and metastasis, as well as in cancer-associated thrombosis (CAT). Tyrosine kinases are implicated in several intracellular signaling pathways involved in tumor biology, thus tyrosine kinase inhibitors (TKIs) represent an important class of anticancer drugs, based on the concept of targeted therapy. Purpose: The objective of this study is the design and synthesis of analogues of the TKIs imatinib and nilotinib in order to develop tyrosine kinase inhibitors, by investigating their molecular requirements, which would express antiplatelet properties. Methods: Based on a recently described by us improved approach in the preparation of imatinib and/or nilotinib analogues, we designed and synthesized in five-step reaction sequences, 8 analogues of imatinib (I–IV), nilotinib (V, VI) and imatinib/nilotinib (VII, VIII). Their inhibitory effects on platelet aggregation and P-selectin membrane expression induced by arachidonic acid (AA), adenosine diphosphate (ADP) and thrombin receptor activating peptide-6 (TRAP-6), in vitro, were studied. Molecular docking studies and calculations were also performed. Results: The novel analogues V–VIII were well established with the aid of spectroscopic methods. Imatinib and nilotinib inhibited AA-induced platelet aggregation, exhibiting IC50 values of 13.30 μΜ and 3.91 μΜ, respectively. Analogues I and II exhibited an improved inhibitory activity compared with imatinib. Among the nilotinib analogues, V exhibited a 9-fold higher activity than nilotinib. All compounds were less efficient in inhibiting platelet aggregation towards ADP and TRAP-6. Similar results were obtained for the membrane expression of P-selectin. Molecular docking studies showed that the improved antiplatelet activity of nilotinib analogue V is primarily attributed to the number and the strength of hydrogen bonds. Conclusion: Our results show that there is considerable potential to develop synthetic analogues of imatinib and nilotinib, as TKIs with antiplatelet properties and therefore being suitable to target cancer progression and metastasis, as well as CAT by inhibiting platelet activation.

Synthesis and biological evaluation of phenyl-amino-pyrimidine and indole/oxindole conjugates as potential BCR-ABL inhibitors

Abstract: Indole/isatin conjugated phenyl-amino-pyrimidine derivatives have been synthesized, characterized and evaluated in vitro for their potential as BCR-ABL inhibitors. Among the series, all derivatives (7a–7o) were found to be more cytotoxic than standard Imatinib against K-562 cell line. Compound 7l was the most active in the series with almost two folds more potency than imitanib (IC50 0.65 μM). In vitro enzymatic studies with recombinant ABL kinase enzyme exhibited promising inhibition in the range of 30–71 μM for most of these novel conjugates. In addition, modelling and other computational studies have been carried out to draw insight into the BCR-ABL protein interactions with the target molecules and drug like properties of the conjugates, respectively. [Figure not available: see fulltext.].

Imatinib derivative as well as preparation method and application thereof

The invention discloses an imatinib derivative. The chemical name of the imatinib derivative is (E)-1-(3,5-dibromobenzyl)-4-(4-methyl-3-(4-(pyridine-3-yl)pyrimidine-2-amino)phenyl)semicarbazide, and the structural formula of the derivative is shown in the description, wherein R is 3,5-dibromobenzyl. The invention further discloses a preparation method of the imatinib derivative. The preparation ofthe imatinib derivative with a new structure is disclosed and the derivative has certain antitumor activity; the preparation method of the compound is also disclosed, the reaction cost is low, the yield is high, the reaction process is simple and easy to control, and the preparation method is suitable for industrial production.

N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative with medicine activity, and preparation method thereof

The invention discloses an N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative with medicine activity, and a preparation method thereof, and belongs to the technical field of medicine synthesis. The structural formula of the N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative with medicine activity is shown in the description. The invention also discloses a preparation method for the N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative with anti-cancer activity. The N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine derivative prepared with the preparation method has good inhibition activity for lung carcinoma cells A549, and has a potential for becoming an anti-tumor medicine.

Design, synthesis and anti-inflammatory activity of pyrimidine scaffold benzamide derivatives as epidermal growth factor receptor tyrosine kinase inhibitors

Novel serious of pyrimidine scaffold benzamide derivatives (9 a-k) were synthesized and characterized by IR, HRMS, and NMR. Docking study of compounds 9 g, 9 h exhibited H-bonding interacts with Met769 into ATP binding site of EGFR-TK which showed similar binding mode to Lapitinib (PDB code: 1M17). Results indicated the ability to potent and selective inhibitors of the Epidermal Growth Factor Receptor tyrosine kinase (EGFR-TK). The molecular electrostatic potential (MEP), frontier molecular orbitals (FMOs) and HOMO-LUMO energy gap of the title compounds were investigated by using the B3LYP/6-31G method. The synthesized compounds were screened for in vitro anti-inflammatory activity.

Design, Synthesis, and Evaluation of the Kinase Inhibition Potential of Pyridylpyrimidinylaminophenyl Derivatives

In view of potent kinase inhibitors for the treatment of myriad human disorders, we synthesized some structurally variant amide/cyclic amide derivatives based on pyridylpyrimidinylaminophenyl amine, the key pharmacophore of the kinase inhibitor drug molecule, imatinib, and evaluated their kinase inhibition potency. Among the various synthesized amides, compound 20, a cyclic amide/pyridin-2(1H)-one derivative, exhibited an IC50 value comparable to that of the drug imatinib against c-Src kinase, and another compound (14) containing a 2-((4-methyl-2-oxo-2H-chromen-6-yl)oxy)acetamide demonstrated an IC50 value of 8.39 μM. Furthermore, the constitution of the cyclic amide derivative was confirmed by the single-crystal X-ray diffraction technique. These results may serve as a gateway for developing novel next-generation kinase inhibitors.

An optimized approach in the synthesis of imatinib intermediates and analogues

We revisited the classical synthetic procedure for imatinib synthesis providing an improved and optimized approach in the preparation of a series of new imatinib analogues. The proposed methodology effectively overcomes certain problematic steps, saves time and labor, provides a very high yield and purity and has the potential to be used for the synthesis of many analogues. The formation of the desired guanidine salt 4, one of the key steps to the imatinib synthesis, was proceeded almost quantitatively by the reaction of the hydrochloride of the suitable aniline 3 with excess of molten cyanamide, without any solvent. Pure arylamine intermediates 6a-d were obtained quantitatively in a short reaction time after reduction of the nitro group of the intermediate pyrimidines 5a-d with hydrogen over the Adam's catalyst. In addition, the application of this optimized approach can be extended in the synthesis of nilotinib and its analogues intermediates.