16097-60-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-chloro-6-trifluoromethyl-pyrimidine is utilized as an intermediate in the synthesis of various pharmaceuticals. Its unique structural features contribute to the development of novel therapeutic agents with potential applications in treating a range of diseases.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Amino-4-chloro-6-trifluoromethyl-pyrimidine serves as a key component in the production of pesticides and herbicides. Its incorporation into these chemicals enhances their effectiveness in controlling pests and weeds, thereby improving crop yields and quality.
Used in Organic Synthesis:
2-Amino-4-chloro-6-trifluoromethyl-pyrimidine is employed as a versatile building block in organic synthesis. Its reactivity and functional group compatibility make it suitable for the preparation of a wide array of organic compounds, including complex molecules with diverse applications.
Used in Industrial Chemical Production:
Beyond its applications in pharmaceuticals and agrochemicals, 2-Amino-4-chloro-6-trifluoromethyl-pyrimidine also finds use in the manufacturing of other industrial chemicals. Its unique properties allow for the creation of specialized compounds tailored for specific applications in various industries.

InChI:InChI=1/C5H3ClF3N3/c6-3-1-2(5(7,8)9)11-4(10)12-3/h1H,(H2,10,11,12)

Upstream product

• 16097-64-6 2,4-dichloro-6-(trifluoromethyl)-pyrimidine 
• 1513-69-5 2-amino-4-hydroxy-6-(trifluoromethyl)pyrimidine 
• 368-54-7 6-trifluoromethyl-4-hydroxy-2-mercaptopyrimidine 
• 85730-34-3 4-Chloro-6-trifluoromethylpyrimidin-2-yldichlorophosphate 
• 85730-37-6 4-Amino-6-trifluoromethylpyrimidin-2-ol Hydrochloride 
• 672-45-7 6-Trifluoromethyluracil 
• 16097-62-4 4-hydroxy-2-(methylthio)-6-(trifluoromethyl)pyrimidine 

Downstream Products

• 16097-61-3 2-Amino-4-methoxy-6-trifluor-methylpyrimidin 
• 913817-52-4 N-[4-(2-amino-4-trifluormethylpyrimidin-6-yloxymethyl)-benzyl]-2,2,2-trifluoro-acetamide 
• 869335-05-7 N₄-{3-Fluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)amino]phenyl}-6-(trifluoromethyl)pyrimidine-2,4-diamine 

Relevant academic research and scientific papers

Discovery and SAR of 6-alkyl-2,4-diaminopyrimidines as histamine H 4 receptor antagonists

This report discloses the discovery and SAR of a series of 6-alkyl-2-aminopyrimidine derived histamine H4 antagonists that led to the development of JNJ 39758979, which has been studied in phase II clinical trials in asthma and atopic dermatitis. Building on our SAR studies of saturated derivatives from the indole carboxamide series, typified by JNJ 7777120, and incorporating knowledge from the tricyclic pyrimidines led us to the 6-alkyl-2,4-diaminopyrimidine series. A focused medicinal chemistry effort delivered several 6-alkyl-2,4-diaminopyrimidines that behaved as antagonists at both the human and rodent H4 receptor. Further optimization led to a panel of antagonists that were profiled in animal models of inflammatory disease. On the basis of the preclinical profile and efficacy in several animal models, JNJ 39758979 was selected as a clinical candidate; however, further development was halted during phase II because of the observation of drug-induced agranulocytosis (DIAG) in two subjects.

Synthesis and in vitro antitumor activity of novel diaryl urea derivatives

A series of novel diaryl ureas containing 4-[(2-amino-6-trifluromethyl) pyrimidine-4-yl]piperazine-1-yl group were synthesized and evaluated for their cytotoxic activities in a panel of human cancer cell lines. Compared with the reference drug Sorafenib, some compounds showed more potent and a broader spectrum of anti-cancer activities. Among them, compound 2p demonstrated significant inhibitory activities against MDA-MB-231, HT-29 and MCF-7 cell lines with IC50 values of 0.016, 0.63, 0.001 μmol/L, respectively.

Pyrimidine derivatives and their use for controlling undesired plant growth

Pyrimidine derivatives and their use for controlling undesired plant growth Compounds of the formula (I) and their use in the field of crop protection are described.

PYRIMIDINES REACTING WITH O6-ALKYLGUANINE-DNA ALKYLTRANSFERASE

The invention relates to pyrimidines suitable as substrates for O6-alkylguanine-DNA alkyltransferases (AGT) of formula (I) wherein R1 is hydrogen, lower alkyl, halogen, cyano, trifluoromethyl or azido; R2 is a linker; and L is a label or a plurality of same or different labels. The invention further relates to methods of transferring a label from pyrimidines of formula (I) to O6-alkylguanine-DNA alkyltransferases (AGT) and AGT fusion proteins.

New fluoro intermediates for herbicidal sulfonylureas

New pyrimidine and triazine intermediates for herbicidal sulfonylureas are prepared as follows: 2,4-dichloro-6-methylpyrimidine is converted via a halogenation, halogen exchange and substitution sequence to 2-amino-4-trifluoromethyl-6-trifluoromethoxypyrimidine. New fluoromethyl-triazines are available starting from guanidine, trichloroacetonitrile and difluoroacetic anhydride, or alternatively from thiocarbamoyl guanidine and chlorodifluoroacetic ester ring closure. To obtain new o-fluoroalkyl-benzenesulfonamide precursors, o-chlorobenzaldehyde was fluorinated with sulfur tetrafluoride, or a bromobenzene derivative was subjected to a substitution reaction with sodium pentafluoropropionate. Sulfonylureas derived from trifluoromethylpyrimidines with an m-methylthio substituent are selective post-emergence herbicides in cotton, presumably due to sulfone metabolization. Selectivity in wheat is obtained by combining 4-methoxy-6-trifluoromethyl-pyrimidine with a lipophilic difluoromethylbenzenesulfonamide moiety. Also in the difluoromethyl-triazine series, the combination with the difluoromethyl-benzenesulfonamide moiety is a good choice for wheat selectivity. Chlorodifluoromethyl- and trifluoromethyltriazines, however, combine better with an aromatic ester for best activity and selectivity in wheat. Selected compounds are undergoing broad field tests in wheat.

ARYL PYRIMIDINE DERIVATIVES

The disclosed pyrimidine derivatives, and pharmaceutically acceptable salts and N-oxides thereof, exhibit useful pharmacological properties, in particular use as selective 5HT 2B-antagonists. The invention is also directed to formulations and methods for treatment.

ARYL PYRIMIDINE DERIVATIVES AND USES THEREOF

The aryl pyrimidine derivatives and pharmaceutically acceptable salts and N-oxides thereof, exhibit useful pharmacological properties, including utility as selective 5HT 2B-antagonists. The 5-HT 2B antagonist is a compound of the formula: STR1 wherein: R. sup.1 is hydrogen, alkyl, lower alkoxy, hydroxyalkyl, cycloalkyl, cycloalkyl lower alkyl, alkenyl, lower thioalkoxy, halo, fluoroalkyl,--NR 6 R. sup.7,--CO 2 R 8,--O(CH 2) n R 9, or lower alkyl optionally substituted with hydroxy, alkoxy, halo, or aryl; in which n is 1, 2, or 3;R 6 and R 7 are hydrogen or lower alkyl; R 8 is hydrogen or lower alkyl; andR 9 is hydrogen, lower alkyl, hydroxy, hydroxy lower alkyl, lower alkenyl, or lower alkoxy;R. sup.2 is hydrogen, lower alkyl, lower alkoxy, halo, or lower fluoroalkyl; R 3 is optionally substituted aryl other than pyridyl, thienyl, or furanyl;R 4 is hydrogen, lower alkyl, cycloalkyl, alkenyl, acyl, amino, amido, aryl,--(CH 2) m NR. sup.10 R 11, or lower alkyl optionally substituted by amino, monosubstituted amino, disubstituted amino, hydroxy, carboxy, aryl, lower alkoxy, amido, alkoxy carbonyl, tetrahydrofuran-2-yl, hydroxyalkoxy, or sulfonamido;in whichR 10 and R. sup.11 are hydrogen or lower alkyl; andR 5 is hydrogen or lower alkyl; provided that: (i) when R 3 is naphthyl, indol-1-yl, or 2,3-dihydroindol-1-yl, and R 2, R 4 and R 5 are all hydrogen, R. sup.1 is not methyl; (ii) when R 3 is phenyl or naphthyl, R 1 is not--NR 6 R 7 ;(iii) when R 3 is phenyl, R 2 is not lower alkoxy, and R 1 and R 2 are not halo;(iv) when R 3 is phenyl and R 1 is H, R 2 is not methyl; and (v) when R 3 is 1,2,3,4-tetrahydroquinolinyl, R 4 and R. sup.5 are hydrogen;or a pharmaceutically acceptable salt or N-oxide thereof.

ARYL PYRIMIDINE DERIVATIVES

The aryl pyrimidine derivatives and pharmaceutically acceptable salts and N-oxides thereof, exhibit useful pharmacological properties, including utility as selective 5HT 2B-antagonists.