5734-62-3

Usage

Uses

Used in Pharmaceutical Industry:
4-chloro-N,N,6-trimethylpyrimidin-2-amine is used as a chemical intermediate in the synthesis of various drugs. Its unique structure allows it to be incorporated into the molecular frameworks of pharmaceutical compounds, contributing to their therapeutic effects.
Used in Agricultural Industry:
In the agricultural sector, 4-chloro-N,N,6-trimethylpyrimidin-2-amine serves as a key ingredient in the production of pesticides. Its chemical properties enable it to be formulated into effective pest control agents, helping to protect crops and ensure agricultural productivity.
The versatility of 4-chloro-N,N,6-trimethylpyrimidin-2-amine in both pharmaceutical and agricultural applications highlights its significance in these industries, showcasing its potential to contribute to the development of new drugs and pesticides.

InChI:InChI=1/C7H10ClN3/c1-5-4-6(8)10-7(9-5)11(2)3/h4H,1-3H3

Upstream product

• 19810-73-2 2-dimethylamino-6-methyl-3H-pyrimidin-4-one 
• 5424-21-5 2,4-dichloro-6-methylpyrimidine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 124-40-3 dimethyl amine 
• 5600-21-5 2-amino-6-methyl-4-chloropyrimidine 
• 74-88-4 methyl iodide 

Downstream Products

• 99357-40-1 2-dimethylamino-4-methylpyrimidine 
• 100383-40-2 dimethyl-(4-vinyl-pyrimidin-2-yl)-amine 

Relevant academic research and scientific papers

Pyrimidyn-Based Dynamin Inhibitors as Novel Cytotoxic Agents

Five focused libraries of pyrimidine-based dynamin GTPase inhibitors, in total 69 compounds were synthesised, and their dynamin inhibition and broad-spectrum cytotoxicity examined. Dynamin plays a crucial role in mitosis, and as such inhibition of dynamin was expected to broadly correlate with the observed cytotoxicity. The pyrimidines synthesised ranged from mono-substituted to trisubstituted. The highest levels of dynamin inhibition were noted with di- and tri- substituted pyrimidines, especially those with pendent amino alkyl chains. Short chains and simple heterocyclic rings reduced dynamin activity. There were three levels of dynamin activity noted: 1–10, 10–25 and 25–60 μM. Screening of these compounds in a panel of cancer cell lines: SW480 (colon), HT29 (colon), SMA (spontaneous murine astrocytoma), MCF-7 (breast), BE2-C (glioblastoma), SJ-G2 (neuroblastoma), MIA (pancreas), A2780 (ovarian), A431 (skin), H460 (lung), U87 (glioblastoma) and DU145 (prostate) cell lines reveal a good correlation between the observed dynamin inhibition and the observed cytotoxicity. The most active analogues (31 a,b) developed returned average GI50 values of 1.0 and 0.78 μM across the twelve cell lines examined. These active analogues were: N2-(3-dimethylaminopropyl)-N4-dodecyl-6-methylpyrimidine-2,4-diamine (31 a) and N4-(3-dimethylaminopropyl)-N2-dodecyl-6-methylpyrimidine-2,4-diamine (31 b).

Discovery and Characterization of Selective and Ligand-Efficient DYRK Inhibitors

Dual-specificity tyrosine-regulated kinase 1A (DYRK1A) regulates the proliferation and differentiation of neuronal progenitor cells during brain development. Consequently, DYRK1A has attracted interest as a target for the treatment of neurodegenerative diseases, including Alzheimer's disease (AD) and Down's syndrome. Recently, the inhibition of DYRK1A has been investigated as a potential treatment for diabetes, while DYRK1A's role as a mediator in the cell cycle has garnered interest in oncologic indications. Structure-activity relationship (SAR) analysis in combination with high-resolution X-ray crystallography leads to a series of pyrazolo[1,5-b]pyridazine inhibitors with excellent ligand efficiencies, good physicochemical properties, and a high degree of selectivity over the kinome. Compound 11 exhibited good permeability and cellular activity without P-glycoprotein liability, extending the utility of 11 in an in vivo setting. These pyrazolo[1,5-b]pyridazines are a viable lead series in the discovery of new therapies for the treatment of diseases linked to DYRK1A function.

Pyrimidine-Based Inhibitors of Dynamin I GTPase Activity: Competitive Inhibition at the Pleckstrin Homology Domain

The large GTPase dynamin mediates membrane fission during clathrin-mediated endocytosis (CME). The aminopyrimidine compounds were reported to disrupt dynamin localization to the plasma membrane via the PH domain and implicate this mechanism in the inhibition of CME. We have used a computational approach of binding site identification, docking, and interaction energy calculations to design and synthesize a new library of aminopyrimidine analogues targeting site-2 of the pleckstrin homology (PH) domain. The optimized analogues showed low micromolar inhibition against both dynamin I (IC50 = 10.6 ± 1.3 to 1.6 ± 0.3 μM) and CME (IC50(CME) = 65.9 ± 7.7 to 3.7 ± 1.1 mM), which makes this series among the more potent inhibitors of dynamin and CME yet reported. In CME and growth inhibition cell-based assays, the data obtained was consistent with dynamin inhibition. CEREP ExpresS profiling identified off-target effects at the cholecystokinin, dopamine D2, histamine H1 and H2, melanocortin, melatonin, muscarinic M1 and M3, neurokinin, opioid KOP and serotonin receptors.

PYRIMIDINE DERIVATIVES AND METHODS OF TREATMENT RELATED TO THE USE THEREOF

The present invention encompasses novel substituted pyrimidine compounds of Formula (I): which act as MCH receptor antagonists. These compounds are useful in pharmaceutical compositions whose use includes prophylaxis or treatment of improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure, obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia, myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disorder, substance abuse disorders and dyskinesias including Parkinson’s disease, epilepsy, and addiction.

Study on the preparation of heteroaryl substituted enamines. A simple synthesis of heteroaryl substituted acetaldoximes from enamines

A comparative study of the reactivity of methyl groups towards N,N-dimethylformamide dimethyl acetal and tert-butoxybis(dimethylamino)methane was carried out on methyl substituted six-membered nitrogen containing heterocycles 1 to give enamines 2, which were easily transformed to oximes by treating with hydroxylamine hydrochloride in methanol. Most of them were isolated as (E,Z)-oximes of heteroarylacetaldehyde (11), but 5-(1,2,4-triazinyl) substituted derivatives as (E,Z)-oximes of 2,5-dihydro-1,2,4-triazin-(Z)-5-ylideneacetaldehyde (11t, 11u, and 12). Oximes were finally transformed to the corresponding acetonitriles 16 and 3-(dimethylamino)acrylonitriles 17.