15755-15-4

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 21, p. 65, 1984 DOI: 10.1002/jhet.5570210115

InChI:InChI=1/C11H11N3/c1-8-7-10(14-11(12)13-8)9-5-3-2-4-6-9/h2-7H,1H3,(H2,12,13,14)

Upstream product

• 113-00-8 guanidine nitrate 
• 93-91-4 1-phenylbutan-1,3-dione 
• 593-85-1 diguanidine carbonate 
• 106124-30-5 4-Methyl-1-oxy-6-phenyl-pyrimidin-2-ylamine 
• 70769-72-1 1-phenyl-3-ethylsulfenyl-2-buten-1-one 
• 58006-77-2 4,7-dihydro-7-methyl-5-phenyl-1,2,4-oxadiazepin-3(2H)-one 
• 420-04-2 CYANAMID 
• 50-01-1 guanidine hydrochloride 
• 98-86-2 acetophenone 
• 30570-19-5 (4RS)-(±)-3,4-dihydro-6-methyl-4-phenylpyrimidine-2(1H)-thione 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 89242-72-8 4-Methyl-2-methylthio-6-phenylpyrimidin-hydroiodid 
• 27955-44-8 2-mercapto-6-methyl-4-phenylpyrimidine 
• 106124-27-0 3-(5-methyl-[1,2,4]oxadiazol-3-ylamino)-1-phenyl-but-2-en-1-one 

Downstream Products

• 857621-22-8 N-acetyl-sulfanilic acid-(4-methyl-6-phenyl-pyrimidin-2-ylamide) 
• 85658-60-2 2-amino-6-methyl-4-phenylpyrimidine 1-oxide 
• 78664-23-0 2-chloro-6-methyl-4-phenylpyrimidine 1-oxide 
• 1104066-55-8 2-(2,6-dibromophenyl)-3-(4-methyl-6-phenylpyrimidin-2-yl)thiazolidin-4-one 
• 663955-81-5 5-iodo-4-methyl-6-phenyl-2-pyrimidinamine 

Relevant academic research and scientific papers

Synthesis and evaluation of 2-(2,6-dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one analogues as anti-HIV-1 agents

A series of 2-(2,6-dihalophenyl)-3-(substituted pyrimidinyl)-1,3-thiazolidin-4-ones were designed on the prediction of quantitative structure-activity relationship (QSAR) studies, synthesized, and evaluated as HIV-1 reverse transcriptase inhibitors. Our attempts in correlating the identified molecular surface features related properties for modeling the HIV-1 RT inhibitory activity resulted in some statistically significant QSAR models with good predictive ability. The results showed that compounds 4m and 4n were highly active in inhibiting HIV-1 replication with EC50 values in the range of 22-28 nM in MT-4 as well as in CEM cells with selectivity indexes of >10,000. The derived models collectively suggest that the compounds should be compact without bulky substitution on its peripheries for better HIV-1 RT inhibitory activity. These models also indicate a preference for hydrophobic compounds to obtain good HIV-1 RT inhibitory activity.

New 2-aminopyrimidine derivatives and their antitrypanosomal and antiplasmodial activities

Abstract: Novel 2-aminopyrimidine derivatives were prepared from acyclic starting materials, benzylidene acetones and ammonium thiocyanates, via 5 steps, including ring closure, aromatization, S-methylation, oxidation to methylsulfonyl compounds, and formation of guanidines with suitable amines. The prepared compounds differ from each other by the substitutions of their amino group and of their phenyl ring. The 2-aminopyrimidines were tested by use of microplate assays for their in vitro activities against a causative organism of sleeping sickness, Trypanosoma brucei rhodesiense, as well as against a causative organism of malaria, Plasmodium falciparum NF54. Their cytotoxic properties were determined with L-6 cells (rat skeletal myoblasts). Some of the compounds exhibited quite good antitrypanosomal activity, and others showed excellent antiplasmodial activity. The influence of the structural modifications on these activities is discussed. Graphic abstract: [Figure not available: see fulltext.].

Cyclization of Ketones with Nitriles under Base: A General and Economical Synthesis of Pyrimidines

A facile, general, and economical synthesis of diversely functionalized pyrimidines has been realized under basic conditions via the copper-catalyzed cyclization of ketones with nitriles. The reaction proceeds via a novel pathway involving the nitriles ac

Microwave-expedited one-pot, two-component, solvent-free synthesis of functionalized pyrimidines

The synthesis of a series of diversely substituted pyrimidines under solvent-free conditions in good yields is described. Under microwave irradiation, a variety of nucleophilic substrates containing the N?C?N unit with ?-dicarbonyl compounds, ethyl cyanoacetate, malononitrile, and chalcones was cyclized to give pyrimidines. A combinatorial type approach for a one-step synthesis has been developed where a ring-closing condensation is followed by spontaneous aromatization to afford 28 functionalized and aryl/alkyl substituted pyrimidines. CSIRO 2007.

THE REACTION OF β-AMINOENONES WITH CYANAMIDE. A HIGH EFFICIENT SYNTHESIS OF 2-AMINOPIRIMIDINES.

β-aminoenones react with cyanamide, molar ratio 1:2, to yield 2-aminopyrimidines in nearly quantitative yields.

Heterocyclic Rearrangements: Rearrangement of N-(1,2,4-Oxadiazol-3-yl)-β-enamino Ketones into Pyrimidine N-Oxides

The behaviour of N-(5-R-1,2,4-oxadiazol-3-yl)-β-enamino ketones towards rearrangement has been investigated.In the presence of anionic reagents in ethanol solution, they rearrange to pyrimidine N-oxides.The synthesis and hydrolytic ring opening of a oxadiazolopyrimidinium system is also reported.

Reactions of β-Sulfenyl α,β-Unsaturated Ketones with Guanidine, Amidines and Diamines

β-Sulfenyl α,β-unsaturated ketones 1a-c reacted with guanidine or amidines to give pyrimidine derivatives 3 in 14-76percent yields.Treatment of ketones 1 with diamines such as ethylenediamine and o-phenylenediamine afforded the seven-membered heterocycles, 2,3-dihydro-1,4-diazepine 5 and 2,3-benzo-1,4-diazepines 8a-c.

REACTIVITY OF 4,7-DIHYDRO-5-PHENYL-1,2,4-OXADIAZEPIN-3(2H)-ONES

The reactions of 4,7-dihydro-5-phenyl-1,2,4-oxadiazepin-3(2H)-ones have been studied.The behaviour of this unsaturated, seven-membered heterocyclic series, which possesses an O-NH-CO-NH functionality, depends on the reagents employed, the experimental con