20980-22-7

Usage

Chemical Properties

clear yellow liquid after melting

Uses

Different sources of media describe the Uses of 20980-22-7 differently. You can refer to the following data:
1. The major metabolite of Tandospirone.
2. 2-(1-Piperazinyl)pyrimidine
3. 2-(1-Piperazinyl)pyrimidine (Buspirone EP Impurity A) is the major metabolite of Tandospirone (T006430).

Synthesis Reference(s)

The Journal of Organic Chemistry, 18, p. 1484, 1953 DOI: 10.1021/jo50017a004

General Description

1-(2-Pyrimidyl)piperazine is a piperazine-based derivative. It is a metabolite of buspirone.

InChI:InChI=1/C8H12N4/c1-2-10-8(11-3-1)12-6-4-9-5-7-12/h1-3,9H,4-7H2/p+1

Upstream product

• 110-85-0 piperazine 
• 1722-12-9 2-chloropyrimidine 
• 99931-83-6 ethyl 4-(2-pirymidinyl)-1-piperazinecarboxylate 
• 127264-76-0 tetra-methoxypropane 
• 75-09-2 dichloromethane 
• 7732-18-5 water 
• 109-12-6 2-aminopyrimidine 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 334-22-5 N,N-bis(chloro-2-ethyl)amine 
• 780705-64-8 1-piperazinecarboxylic acid 4-(2-pyrimidinyl)-, 1,1-dimethylethyl ester 
• 78069-54-2 1-(2-pyrimidinyl)piperazine hydrochloride 
• 94021-22-4 1-(2-pyrimidyl)piperazine dihydrochloride 

Downstream Products

• 83928-76-1 gepirone 
• 87760-53-0 tandospirone 
• 81461-73-6 8-(2-Pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane Bromide 
• 135704-99-3 1,1-Dioxo-2-[4-(4-pyrimidin-2-yl-piperazin-1-yl)-but-2-ynyl]-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one 
• 135705-03-2 1-[4-(4-Pyrimidin-2-yl-piperazin-1-yl)-but-2-ynyl]-pyrrolidine-2,5-dione 
• 88268-16-0 2-(4-formyl-1-piperazinyl)primidine 
• 3605-01-4 piribedil 
• 36505-84-7 BUSPIRONE 
• 757156-67-5 1-(4-Nitro-phenoxy)-3-(4-pyrimidin-2-yl-piperazin-1-yl)-propan-2-ol 
• 105277-52-9 7-[3-(4-Pyrimidin-2-yl-piperazin-1-yl)-propoxy]-chromen-4-one 
• 92584-68-4 <<(pyrimidino-2')-4 piperazinyl-1>-2 ethyl>-6 benzoxazolinone 
• 124673-96-7 (<(pyrimidino-2)-4 piperazinyl-1>-4 butyryl)-6 methyl-3 benzoxazolinone 
• 151021-21-5 3-cyano-2-ethoxy-5-formyl-4-phenyl-6-piperazinyl>pyridine 
• 140438-97-7 2-Phenyl-6-[6-(4-pyrimidin-2-yl-piperazin-1-yl)-hexyloxy]-chromen-4-one 

Relevant academic research and scientific papers

Synthesis of heteroarylpiperazines and heteroarylbipiperidines with a restricted side chain and their affinities for 5-HT1A receptor

Heteroarylpiperazine and heteroarylbipiperidine derivatives, bearing a 4-piperidine ring instead of an alkylamino side chain to give the semi-rigidity, were prepared and evaluated for their abilities to displace [3H] 8-OH-DPAT binding to the rat hippocampal synaptic membranes. These compounds showed low to moderate affinities for 5-HT1A receptor, with Ki values ranging from 6912 nM to 232 nM. Of these compounds, 8 b and 15 e exhibited the best affinities for 5-HT1A receptor with Ki values of 232 nM and 338 nM, respectively.

ANTIVIRAL COMPOUNDS

The invention is provides novel antiviral compounds, as well as derivatives thereof. The compounds of the invention are preferably formulated as pharmaceuticals. The invention provides the compounds for use in the prevention and treatment of infectious diseases, in particular viral diseases. In some aspects the invention is based on the antiviral activity of the provided compounds against the Chikungunya virus, and hence, their application in the treatment or prevention of any physiological manifestation of such viral infection.

Electrophilic Zinc Homoenolates: Synthesis of Cyclopropylamines from Cyclopropanols and Amines

Metal homoenolates, produced via C-C bond cleavage of cyclopropanols, have been extensively investigated as nucleophiles for the synthesis of β-substituted carbonyl derivatives. Herein, we demonstrate that zinc homoenolates can react as carbonyl-electrophiles in the presence of nucleophilic amines to yield highly valuable trans-cyclopropylamines in good yields and high diastereoselectivities. GSK2879552, a lysine demethylase 1 inhibitor currently in clinical trials for the treatment of small cell lung carcinoma, was synthesized using this strategy.

Preparation method of piribedil

The invention provides a preparation method of piribedil. The preparation method comprises the following steps of: preparing piperonyl chloride; preparing piperazinyl pyrimidine; and preparing piribedil. The preparation method of piribedil is simple, low in production cost, high in integral yield of reaction and convenient for industrial production, and has huge promotional meaning.

Synthetic method of piribedil

The invention relates to a synthetic method of piribedil. The synthetic method is a brand new process comprising the steps of synthesizing piperonyl piperazine in one step under the effects of pentamethyleneamine, piperazine pyrimidine and paraformaldehyde, and reacting by virtue of piperonyl piperazine and dichloropyrimidine so as to synthesize piribedil. Piperonyl piperazine has not been synthesized by virtue of the synthetic method before. Compared with a traditional synthetic method of piribedil, the synthetic method has the advantages that synthetic steps are simplified, the three wastes are reduced, the utilization ratio of pentamethyleneamine is remarkably increased, and the after-treatment is relatively environment-friendly.

Preparation method of high-quality piribedil

The invention provides a preparation method of high-quality piribedil. The preparation method of the high-quality piribedil comprises preparation of piperonyl chloride, preparation of piperazinyl pyrimidine and preparation of piribedil. The method is simple and brief, the production cost is low, the reaction overall yield is high, industrialized production is facilitated, and great popularization significance is achieved.

Syntheses, biological activities and SAR studies of novel carboxamide compounds containing piperazine and arylsulfonyl moieties

A series of novel carboxamide compounds 19a-19j, 20a-20j and 22a-22d containing piperazine and arylsulfonyl moieties have been synthesized. The bioassay results showed that some compounds exhibited favorable herbicidal activities against dicotyledonous plants and many of them possessed excellent antifungal activities. Among 24 novel compounds, some showed superiority over the commercial fungicides Chlorothalonil, Dimethomorph, Thiophanate-methyl, Iprodione, and Zhongshengmycin at 500 mg/L concentration. Some compounds also exhibited high KARI inhibitory activity at 100 γ1/4g/mL concentration and could be used as new KARI lead inhibitors for further studies. Moreover, SAR of these new compounds were comprehensively investigated using different computational methods in which 3D-QSAR model obtained provided useful information for further structural optimization for the discovery of new fungicides. The results of this research will contribute to explore comprehensive biological activities of piperazine-containing compounds in different areas of chemistry.

Pd-Catalyzed Synthesis of Piperazine Scaffolds under Aerobic and Solvent-Free Conditions

A facile Pd-catalyzed methodology providing an efficient synthetic route to biologically relevant arylpiperazines under aerobic conditions is reported. Electron donating and sterically hindered aryl chlorides were aminated to afford yields up to 97%, with examples using piperazine as solvent, illustrating an ecofriendly, cost-effective synthesis of these privileged structures.

Chrysin-piperazine conjugates as antioxidant and anticancer agents

Synthesis of 7-(4-bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one intermediate treating chrysin with 1,4-dibromobutane facilitated combination of chrysin with a wide range of piperazine moieties which were equipped via reacting the corresponding amines with bis(2-chloroethyl)amine hydrochloride in diethylene glycol monomethyl ether solvent. Free radical scavenging potential of prepared products was analyzed in vitro adopting DPPH and ABTS bioassay in addition to the evaluation of in vitro anticancer efficacies against cervical cancer cell lines (HeLa and CaSki) and an ovarian cancer cell line SK-OV-3 using SRB assay. Bearable toxicity of 7a-w was examined employing Madin-Darby canine kidney (MDCK) cell line. In addition, cytotoxic nature of the presented compounds was inspected utilizing Human bone marrow derived mesenchymal stem cells (hBM-MSCs). Overall, 7a-w indicated remarkable antioxidant power in scavenging DPPH+ and ABTS++, particularly analogs 7f, 7j, 7k, 7l, 7n, 7q, 7v, 7w have shown promising free radical scavenging activity. Analogs 7j and 7o are identified to be highly active candidates against HeLa and CaSki cell lines, whereas 7h and 7l along with 7j proved to be very sensitive towards ovarian cancer cell line SKOV-3. None of the newly prepared scaffolds showed cytotoxic nature toward hBM-MSCs cells. From the structure-activity point of view, nature and position of the electron withdrawing and electron donating functional groups on the piperazine core may contribute to the anticipated antioxidant and anticancer action. Different spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, Mass) and elemental analysis (CHN) were utilized to confirm the desired structure of final compounds.

Synthesis and Biological Activity of Novel Furan/Thiophene and Piperazine-Containing (Bis)1,2,4-triazole Mannich Bases

Series of novel furan/thiophene and piperazine-containing 1,2,4-triazole Mannich bases and bis(1,2,4-triazole) Mannich bases have been conveniently synthesized via Mannich reaction with triazole Schiff bases, various piperazine derivatives, and formaldehyde as intermediates in good yields. Their structures were characterized by melting points, 1H NMR, 13C NMR, IR and elemental analysis. The preliminary bioassay showed that most compounds exhibited significant in vitro and in vivo fungicidal activity against several test plant fungi. Among 32 new compounds, the trifluoromethyl-containing compounds showed superior activity than the methyl-containing ones. Several compounds, such as F8, F9, F10, G5, H7, H8, I3 and I4, were comparable with some commercial fungicides against different fungi during the present study and could be further structurally optimized. Meanwhile, several compounds showed good herbicidal activity against Brassica campestris at 100 μg/mL and KARI inhibitory activity at 200 μg/mL. However, compounds exhibited poor insecticidal activity against oriental armyworm at 200 μg/mL in the preliminary studies. The research results will provide useful information for the design and discovery of new agrochemicals with novel heterocyclic structures.