20551-34-2

Basic information

• Product Name: 5-Chloro-2,6-dimethyl-4(3H)-pyrimidone
• Synonyms: 5-Chloro-2,6-dimethyl-4(3H)-pyrimidone;5-Chloro-2,6-dimethylpyrimidin-4-ol
• CAS NO: 20551-34-2
• Molecular Formula: C₆H₇ClN₂O
• Molecular Weight: 158.59
• Mol File: 20551-34-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 201 °C
• Boiling Point: 217.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.38±0.1 g/cm3(Predicted)
• PKA: 8.11±0.50(Predicted)
• CAS DataBase Reference: 5-Chloro-2,6-dimethyl-4(3H)-pyrimidone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2,6-dimethyl-4(3H)-pyrimidone(20551-34-2)
• EPA Substance Registry System: 5-Chloro-2,6-dimethyl-4(3H)-pyrimidone(20551-34-2)

Safety Data

• Hazardous Substances Data: 20551-34-2(Hazardous Substances Data)

Upstream product

• 124-42-5 acetamidine hydrochloride 
• 609-15-4 ethyl 2-chloro-3-oxo-butyrate 
• 4755-81-1 methyl 2-chloroacetoacetate 
• 143-37-3 acetamidine 
• 932-72-9 (Dichloroiodo)benzene 
• 6622-92-0 4-hydroxy 2,6-dimethylpyrimidine 

Downstream Products

• 105742-66-3 4,5-dichloro-2,6-dimethylpyrimidine 

Relevant articles and documents

Design, synthesis, and insecticidal/acaricidal evaluation of novel pyrimidinamine derivatives containing phenyloxazole moiety

A series of novel pyrimidinamine derivatives containing phenyloxazole moiety were designed and synthesized, and their structures were characterized by 1H NMR, MS, and elemental analyses. The bioassay results displayed that some compounds exhibited remarkable insecticidal activities against Aphis fabae and Tetranychus cinnabarinus. Especially, 5-chloro-6-ethyl-2-methyl-N-((2-(p-tolyl)oxazol-4-yl)methyl)pyrimidin-4-amine (9o) showed potent activity against A. fabae, superior to that of the commercial insecticide, imidacloprid. In addition, 5-chloro-6-ethyl-2-methyl-N-((2-(4-(trifluoromethyl)phenyl)oxazol-4-yl)methyl)pyrimidin-4-amine (9r) showed potent activities against T. cinnabarinus, inferior to that of the commercial insecticide spirotetramat. The structure–activity relationship study for the target compounds was also discussed.

Design, synthesis and fungicidal activity evaluation of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety

Diflumetorim is a member of pyrimidinamine fungicides that possess excellent antifungal activities. Nevertheless, as reported that the activity of diflumetorim to corn rust (Puccinia sorghi) was not ideal (EC50 = 53.26 mg/L). Herein, a series of novel pyrimidinamine derivatives containing phenyl-thiazole/oxazole moiety were designed based on our previous study and the structural characteristics of diflumetorim, synthesized and bioassayed to discover novel fungicides with excellent antifungal activities. Among these compounds, T18 gave the optimal fungicidal activity, which respectively offers control effects with EC50 values of 0.93 mg/L against P. sorghi and 1.24 mg/L against E. graminis, significantly superior to commercial fungicides diflumetorim, tebuconazole, and flusilazole. Cell cytotoxicity results suggested that compound T18 has lower toxicities than diflumetorim. Furthermore, DFT calculation indicated that the phenyl-thiazole/oxazole moiety plays an unarguable role in the improvement of activity, which will contribute to designing and developing more potent compounds in the future.

Synthesis and biological evaluation of novel sigma-1 receptor antagonists based on pyrimidine scaffold as agents for treating neuropathic pain

The discovery and synthesis of a new series of pyrimidines as potent sigma-1 receptor (σ1R) antagonists, associated with pharmacological antineuropathic pain activity, are the focus of this article. The new compounds were evaluated in vitro in σ-1 and σ-2 receptor binding assays. The nature of the pyrimidine scaffold was crucial for activity, and a basic amine was shown to be necessary according to the known pharmacophoric model. The most promising derivative was 5-chloro-2-(4-chlorophenyl)-4-methyl-6-(3-(piperidin-1-yl)propoxy)pyrimidine (137), which exhibited a high binding affinity to σ1R receptor (Ki σ1 = 1.06 nM) and good σ-1/2 selectivity (1344-fold). In in vivo tests, compound 137 exerted dose-dependent antinociceptive effects in mice formalin model and rats CCI models of neuropathic pain. In addition, no motor impairments were found in rotarod tests; acceptable pharmacokinetic properties were also noted. These data suggest compound 137 may constitute a novel class of drugs for the treatment of neuropathic pain.