5734-62-3

Basic information

• Product Name: 4-chloro-N,N,6-trimethylpyrimidin-2-amine
• Synonyms: 4-chloro-N,N,6-trimethylpyrimidin-2-amine;4-Chloro-N,N,6-trimethyl-2-pyrimidinamine;(4-chloro-6-methyl-pyrimidin-2-yl)-dimethyl-amine;2-dimethylamino-4-chloro-6-methylpyrimidine;4-chloro-N,N,6-trimethylpyrimidin-2-amine(SALTDATA: FREE);2-(N,N-Dimethylamino)-4-chloro-6-methylpyrimidine
• CAS NO: 5734-62-3
• Molecular Formula: C₇H₁₀ClN₃
• Molecular Weight: 171.6274
• EINECS: 227-243-7
• Mol File: 5734-62-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 35-36℃
• Boiling Point: 272℃
• Flash Point: 118℃
• Appearance: /
• Density: 1.207
• Vapor Pressure: 0.0062mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 4-chloro-N,N,6-trimethylpyrimidin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-N,N,6-trimethylpyrimidin-2-amine(5734-62-3)
• EPA Substance Registry System: 4-chloro-N,N,6-trimethylpyrimidin-2-amine(5734-62-3)

Safety Data

• Hazardous Substances Data: 5734-62-3(Hazardous Substances Data)

Usage

General Description

4-chloro-N,N,6-trimethylpyrimidin-2-amine is a chemical compound with the molecular formula C7H10ClN3. It is a derivative of pyrimidine and is characterized by a chlorine atom and three methyl groups attached to the pyrimidine ring. 4-chloro-N,N,6-trimethylpyrimidin-2-amine is used predominantly in pharmaceutical and agricultural applications. In the pharmaceutical industry, it is used as an intermediate in the synthesis of various drugs, and in the agricultural industry, it is used as a key ingredient in the production of pesticides. Its chemical structure and properties make it useful in a wide range of applications, contributing to its significance in various industries.

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

Downstream Products

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

Relevant articles and documents

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).

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.

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.