61667-16-1

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzyl-6-chloro-4-pyrimidinamine is used as a chemical intermediate for the synthesis of various pharmaceutical drugs. Its unique structure allows it to be a key component in the creation of new medications.
Used in Anti-Cancer Drug Development:
In the field of oncology, N-Benzyl-6-chloro-4-pyrimidinamine is utilized as a precursor in the development of anti-cancer drugs. Its molecular structure contributes to the design of compounds that can target and combat cancer cells.
Used in Anti-Inflammatory Drug Synthesis:
Beyond oncology, N-Benzyl-6-chloro-4-pyrimidinamine also finds application in the synthesis of anti-inflammatory drugs, where it can be instrumental in managing inflammation-related conditions by contributing to the development of effective pharmaceuticals.
Used in Bioactive Molecule Research:
N-Benzyl-6-chloro-4-pyrimidinamine is also used in research settings for the study of bioactive molecules. Its presence in experimental compounds can provide insights into the mechanisms of action and potential therapeutic effects of new drug candidates.

Upstream product

• 1193-21-1 4,6-dichloropyrimidine 
• 100-46-9 benzylamine 

Downstream Products

• 944062-58-2 N-benzyl-6-chloro-5-nitrosopyrimidin-4-amine 
• 1196993-69-7 N-benzyl-6-(4-methylpiperazin-1-yl)pyrimidin-4-amine 
• 1360179-68-5 N-benzyl-6-chloro-N-nitrosopyrimidin-4-amine 
• 1360179-74-3 N-benzyl-N-nitroso-6-pyrrolidinopyrimidin-4-amine 
• 1360179-76-5 N-benzyl-6-morpholino-N-nitrosopyrimidin-4-amine 
• 1360179-77-6 N-benzyl-(6-morpholino-4-pyrimidinyl)-acetamide 

Relevant academic research and scientific papers

1,4,9-Triazaspiro[5.5]undecan-2-one Derivatives as Potent and Selective METTL3 Inhibitors

N6-methyladenosine (m6A) is the most frequent of the 160 RNA modifications reported so far. Accumulating evidence suggests that the METTL3/METTL14 protein complex, part of the m6A regulation machinery, is a key player in a variety of diseases including several types of cancer, type 2 diabetes, and viral infections. Here we report on a protein crystallography-based medicinal chemistry optimization of a METTL3 hit compound that has resulted in a 1400-fold potency improvement (IC50 of 5 nM for the lead compound 22 (UZH2) in a time-resolved F?rster resonance energy transfer (TR-FRET) assay). The series has favorable ADME properties as physicochemical characteristics were taken into account during hit optimization. UZH2 shows target engagement in cells and is able to reduce the m6A/A level of polyadenylated RNA in MOLM-13 (acute myeloid leukemia) and PC-3 (prostate cancer) cell lines.

Discovery of VX-509 (Decernotinib): A Potent and Selective Janus Kinase 3 Inhibitor for the Treatment of Autoimmune Diseases

While several therapeutic options exist, the need for more effective, safe, and convenient treatment for a variety of autoimmune diseases persists. Targeting the Janus tyrosine kinases (JAKs), which play essential roles in cell signaling responses and can contribute to aberrant immune function associated with disease, has emerged as a novel and attractive approach for the development of new autoimmune disease therapies. We screened our compound library against JAK3, a key signaling kinase in immune cells, and identified multiple scaffolds showing good inhibitory activity for this kinase. A particular scaffold of interest, the 1H-pyrrolo[2,3-b]pyridine series (7-azaindoles), was selected for further optimization in part on the basis of binding affinity (Ki) as well as on the basis of cellular potency. Optimization of this chemical series led to the identification of VX-509 (decernotinib), a novel, potent, and selective JAK3 inhibitor, which demonstrates good efficacy in vivo in the rat host versus graft model (HvG). On the basis of these findings, it appears that VX-509 offers potential for the treatment of a variety of autoimmune diseases.

PYRIMIDINE FGFR4 INHIBITORS

Provided herein are compounds of Formula I useful as FGFR4 inhibitors, as well as methods of use of the same.

The first example of the Fischer-Hepp type rearrangement in pyrimidines

A N-nitroso moiety can be used for the activation of chloropyrimidines toward a nucleophilic substitution reaction with amines. The subsequent treatment of the obtained products with aq H2SO4 can lead to either N-denitrosation to obtain 4,6-pyrimidinediamines or to a Fischer-Hepp type rearrangement to obtain 5-nitroso-4,6-pyrimidinediamines. It was found that the outcome of the reaction strongly depends on the structure of the pyrimidines. Activation of the pyrimidine ring by three groups with a positive mesomeric effect is crucial for the intramolecular nitroso group migration.

Effect of substituent structure on pyrimidine electrophilic substitution: A rebuttal

The report about a series of unexpected and obscure effects influencing the electrophilic nitrosation of activated pyrimidines (Tetrahedron 2007, 63, 5394) was shown to be erroneous. Instead of electrophilic substitution at position 5 of the pyrimidine ring, N-nitrosation of the secondary amino group in the 4-position of the pyrimidine ring took place. Moreover it was shown that the synthetic sequence for the preparation of purines is also incorrect.

Discovery of a series of potent and selective human H4 antagonists using ligand efficiency and libraries to explore structure-activity relationship (SAR)

We describe the identification of a potent, selective lead series that shows antagonism against the human histamine H4 receptor from thirteen actives identified in an HTS as part of a hit to lead program. By focusing on ligand efficiency and concurrently using a diversity based approach, compounds based around 2,4-diaminopyrimidine were identified with compound 25 being quickly shown to be a good lead. It also had the highest ligand efficiency in the series.

2,4-Diaminopyrimidines as histamine H4 receptor ligands-Scaffold optimization and pharmacological characterization

The human histamine H4 receptor (hH4R) is a promising new target in the therapy of inflammatory diseases and disorders of the immune system. For the development of new H4R antagonists a broad ligand-based virtual screening was performed resulting in two hits. The dissection of their common annelated aromatic core into its heteromonocyclic components showed that 2,4-diaminopyrimidine is a potent hH4R affinity scaffold, which was comprehensively investigated. Structure-activity relationship studies revealed that slight structural changes evoke extensive differences in functional activities and potencies: while o- and p-substituted benzyl amines mainly showed partial agonism, m-substituted and rigidified ones exhibited inverse agonist efficacy.

Effect of substituent structure on pyrimidine electrophilic substitution

In an investigation into the electrophilic nitrosation reactions of a series of 4,6-disubstituted pyrimidine derivatives, a subtle interplay between the electronic nature of the C-4 and C-6 substituents and reactivity was found where these were chloro-, mono- or disubstituted amino groups. Effects such as the presence of an aryl group or two alkyl groups on the amino moiety impede the progress of the reaction despite the presence of a second activating group.

Microwave-assisted synthesis of aminopyrimidines

Series of mono- or di-substituted aminopyrimidine derivatives were synthesized through microwave-assisted aromatic nucleophilic substitution or Suzuki coupling.