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Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-methyl-6-(trifluoromethyl)-pyrimidine is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable intermediate in the development of new drugs, particularly in the area of medicinal chemistry.
Used in Agrochemical Industry:
2-Amino-4-methyl-6-(trifluoromethyl)-pyrimidine is used as a key component in the synthesis of agrochemicals, such as pesticides and herbicides. Its presence in these compounds can contribute to their effectiveness in controlling pests and weeds in agricultural settings.
Used in Research and Development:
2-Amino-4-methyl-6-(trifluoromethyl)-pyrimidine is used as a research compound for studying its chemical properties and potential applications in various fields. Its synthesis and characterization can provide insights into the behavior of similar compounds and contribute to the advancement of scientific knowledge.

InChI:InChI=1/C6H6F3N3/c1-3-2-4(6(7,8)9)12-5(10)11-3/h2H,1H3,(H2,10,11,12)

Upstream product

• 367-57-7 1,1,1-Trifluoro-2,4-pentanedione 
• 420-04-2 CYANAMID 
• 594-14-9 guanidinium sulfate 
• 50-01-1 guanidine hydrochloride 
• 135351-20-1 (3E)-1,1,1-trifluoro-4-methoxy-pent-3-en-2-one 
• 113-00-8 guanidine nitrate 
• 877178-95-5 2-amino-6-methyl-4-(trifluoromethyl)pyrimidine 1-oxide 
• 1020540-97-9 4-trifluoromethyl-6-methyl-2-acetylaminopyrimidine 

Downstream Products

• 241164-09-0 2-chloro-6-methyl-4-(trifluoromethyl)pyrimidine 
• 1097721-66-8 2-(2,6-dibromophenyl)-3-(4-methyl-6-trifluoromethylpyrimidin-2-yl)thiazolidin-4-one 

Relevant academic research and scientific papers

One-pot synthesis of N2-aminoprotected 6-substituted and cycloalka[d] 4-trifluoromethyl-2-acetylaminopyrimidines

(Chemical Equation Presented) The one-pot synthesis of a novel series of amino-protected 6-alkyl-, 6-aryl-, 6-heteroaryl- and 5,6-fused-cycloalkane 4-trifluoromethyl-2-acetylaminopyrimidines, where alkyl = Me; aryl = Ph, 4-CH3Ph, 4-FPh, 4-ClPh, 4-BrPh, 4-OCH3Ph, 4-NO 2Ph, 4,4′-biphenyl, 1-naphthyl; heteroaryl = 2-thienyl, 2-furyl and cycloalkyl = c-C6H4, c-C7H5 from the reaction of substituted 4-methoxy-1,1,1-trifluoroalk-3-en-2-ones with 1-acetylguanidine in acetonitrile or propan-2-ol as solvent, is reported. The acetylamino group of 2-acetylaminopyrimidines was hydrolyzed under three different conditions to afford the corresponding free 2-aminopyrimidines.

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.

One-pot synthesis of fluorinated 2-amino-pyrimidine-N-oxides. Competing pathways in the four-atom side-chain rearrangements of 1,2,4-oxadiazoles

Trifluoromethylated 2-amino-pyrimidine N-oxides have been synthesized by reaction of the 3-amino-5-methyl-1,2,4-oxadiazole with trifluoromethyl-β- diketones in the presence of perchloric acid, followed by hydrolysis. In this ring-to-ring transformation an initial formation of (unisolated) 1,2,4-oxadiazole-pyrimidinium salts, and subsequent ring-opening at the oxadiazole moiety occurs. Isolation of 2-(hydroxyamino)-pyrimidine from the reaction mixture evidenced the presence of a competing pathway where the N(4) nitrogen of the oxadiazole is involved in the formation of a regioisomeric pyrimidinium salt. The effect of the trifluoromethyl group on the product distribution is discussed. By X-ray analysis, the crystal structure of two different N-oxide regioisomers has been unambiguously ascertained.

Synthesis of fluorinated heterocycles

Selected 1,3-diketones having a trifluoromethyl group and/or a fluorine in the 2-position were condensed with aromatic hydrazines, hydroxylamine, urea, thiourea, guanidine, and substituted anilines producing pyrazoles, isoxazoles, pyrimidines, and quinolines, respectively, in yields ranging from 27 to 87%.

Haloacetylated Enol Ethers. 8 [12]. Reaction of β-Alkoxyvinyl Trihalomethyl Ketones with Guanidine Hydrochloride. Synthesis of 4-Trihalomethyl-2-Aminopyrimidines

In this work the results of the reaction of β-alkoxyvinyl trihalomethyl ketones 1, 2a-e, with guanidine hydrochloride are reported. Depending on the ketone 1 or 2 and the conditions under which the reactions were carried out, 4-trihalomethyl-2-amino pyrimidines, β-alkoxyvinyl carboxylic acids, or β-acetal carboxylic esters were obtained.

Improved Synthesis of Fluoroalkyl and Fluoroaryl Substituted 2-Aminopyrimidines

Fluoroalkyl and fluoroaryl substituted 2-aminopyrimidines have been prepared in good yields by the cyclization of guanidine salts with fluorine substituted β-diketones in sodium isopropoxide/isopropanol at reflux.