6343-68-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4,6-dichloro-5-ethylpyrimidine is used as a building block for the synthesis of pharmaceuticals, particularly in the development of anti-cancer and anti-inflammatory drugs. Its versatile reactivity and potential biological activity make it an important intermediate in the creation of new medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Amino-4,6-dichloro-5-ethylpyrimidine is utilized as a key component in the synthesis of various agrochemicals. Its unique structure and properties contribute to the development of effective products for agricultural applications.
Used in Organic Synthesis:
2-Amino-4,6-dichloro-5-ethylpyrimidine is employed as an intermediate in organic synthesis due to its diverse reactivity. This allows chemists to create a wide range of organic compounds for various applications, including the production of specialty chemicals and materials.
It is crucial to handle 2-Amino-4,6-dichloro-5-ethylpyrimidine with care, as it can pose hazards if not properly managed and used.

InChI:InChI=1/C6H7Cl2N3/c1-2-3-4(7)10-6(9)11-5(3)8/h2H2,1H3,(H2,9,10,11)

Upstream product

• 30201-72-0 2-amino-5-ethylpyrimidine-4,6-diol 
• 133-13-1 ethyl diethyl malonate 
• 1395342-97-8 4,6-dichloro-5-ethyl-2-{[(dimethylamino)methylene]amino}pyrimidine 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 138915-47-6 5-ethyl-4,6-dimethoxy-pyrimidin-2-ylamine 
• 39268-71-8 2-Amino-5-ethylpyrimidin 
• 6343-69-7 6-chloro-5-ethylpyrimidine-2,4-diamine 
• 73119-06-9 5-ethylpyrimidine-2,4-diamine 
• 857622-77-6 N-acetyl-sulfanilic acid-(5-ethyl-4,6-dimethoxy-pyrimidin-2-ylamide) 

Relevant academic research and scientific papers

Inhibitor development of MTH1 via high-throughput screening with fragment based library and MTH1 substrate binding cavity

MutT Homolog 1 (MTH1) has been proven to hydrolyze oxidized nucleotide triphosphates during DNA repair. It can prevent the incorporation of wrong nucleotides during DNA replication and mitigate cell apoptosis. In a cancer cell, abundant reactive oxygen species can lead to substantial DNA damage and DNA mutations by base-pairing mismatch. MTH1 could eliminate oxidized dNTP and prevent cancer cells from entering cell death. Therefore, inhibition of MTH1 activity is considered to be an anti-cancer therapeutic target. In this study, high-throughput screening techniques were combined with a fragment-based library containing 2,313 compounds, which were used to screen for lead compounds with MTH1 inhibitor activity. Four compounds with MTH1 inhibitor ability were selected, and compound MI0639 was found to have the highest effective inhibition. To discover the selectivity and specificity of this action, several derivatives based on the MTH1 and MI0639 complex structure were synthesized. We compared 14 complex structures of MTH1 and the various compounds in combination with enzymatic inhibition and thermodynamic analysis. Nanomolar-range IC50 inhibition abilities by enzyme kinetics and Kd values by thermodynamic analysis were obtained for two compounds, named MI1020 and MI1024. Based on structural information and compound optimization, we aim to provide a strategy for the development of MTH1 inhibitors with high selectivity and specificity.

5-substituted 2-amino-4,6-dihydroxypyrimidines and 2-amino-4, 6-dichloropyrimidines: Synthesis and inhibitory effects on immune-activated nitric oxide production

A series of 5-substituted 2-amino-4,6-dihydroxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4,6-dihydroxypyrimidine analogs to novel 5-substituted 2-amino-4,6-dichloropyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino- 4,6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4,6- dichloropyrimidine with an IC50 of 2 μM (higher activity than the most potent reference compound) while the IC50s of other derivatives were within the range of 9-36 l M. The 2-amino-4,6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.

5-Substituted 2-amino-4, 6-dihydroxypyrimidines and 2-amino-4, 6-dichloropyrimidines: Synthesis and inhibitory effects on immune-activated nitric oxide production

A series of 5-substituted 2-amino-4, 6-dihydr-oxypyrimidines were prepared by a modified condensation of the corresponding monosubstituted malonic acid diesters with guanidine in an excess of sodium ethoxide. The optimized procedure using Vilsmeier-Haack-Arnold reagent, followed by immediate deprotection of the (dimethylamino)methylene protecting groups, has been developed to convert the 2-amino-4, 6-dihydroxypyrimi-dine analogs to novel 5-substituted 2-amino-4, 6-dichloro-pyrimidines in high yields. Pilot screening for biological properties of the prepared compounds was done in mouse peritoneal cells using the in vitro nitric oxide (NO) assay. Irrespective of the substituent at the 5 position, 2-amino-4, 6-dichloropyrimidines inhibited immune-activated NO production. The most effective was 5-fluoro-2-amino-4, 6-dichloropyrimidine with an IC50 of 2 lM (higher activity than the most potent reference compound) while the IC50s of other derivatives were within the range of 9-36 μM. The 2-amino-4, 6-dihydroxypyrimidine counterparts were devoid of any NO-inhibitory activity. The compounds had no suppressive effects on the viability of cells. The Mechanism of action remains to be elucidated.

PYRIMIDINE COMPOUNDS INHIBITING THE FORMATION OF NITRIC OXIDE AND PROSTAGLANDIN E2, METHOD OF PRODUCTION THEREOF AND USE THEREOF

The invention provides pyrimidine compounds of general formula (I), which reduce simultaneously the production of nitric oxide (NO) and prostaglandin E2 (PGE2). They have no negative effect on the viability of cells in concentrations decreasing the production of these factors by up to 50%; they are not cytotoxic. Furthermore, a method of preparation of the pyrimidine compounds of general formula (I), carrying 2-formamido group, a pharmaceutical composition comprising the substituted pyrimidine compounds according to the invention, and the use of these compounds for the treatment of inflammatory and cancer diseases are provided.˙

BENZOXAZEPINES AS INHIBITORS OF P13K/MTOR AND METHODS OF THEIR USE AND MANUFACTURE

The invention is directed 10 Compound's of Formula I: and pharmaceutically acceptable salts or solvates thereof, as well as methods of making and using the compounds.