2134-36-3

Usage

Uses

Used in Scientific Research:
ETHYL 4-CHLORO-2-METHYLPYRIMIDINE-5-CARBOXYLATE is used as a chemical intermediate for the synthesis of other chemicals. Its role in this application is to serve as a building block or a precursor in the preparation of more complex molecules, which can be further utilized in various fields of research and development.

InChI:InChI=1/C8H9ClN2O2/c1-3-13-8(12)6-4-10-5(2)11-7(6)9/h4H,3H2,1-2H3

Upstream product

• 53135-24-3 ethyl 3,4-dihydro-4-oxo-2-methylpyrimidine-5-carboxylate 
• 53135-24-3 ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 

Downstream Products

• 7389-14-2 2-methyl-4-amino-5-(carboxamidemethyl)pyrimidine 
• 143618-25-1 2-Methyl-4-{propyl-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-pyrimidine-5-carboxylic acid ethyl ester 
• 143618-34-2 4-{Butyl-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-2-methyl-pyrimidine-5-carboxylic acid ethyl ester 
• 83410-35-9 ethyl 2-methyl-4-phenylethynyl-5-pyrimidinecarboxylate 
• 101251-42-7 2-Methyl-4-hydrazino-5-ethoxycarbonyl-pyrimidin 
• 16146-47-7 ethyl 2-methyl-4-(3-trifluoromethylanilino)pyrimidine-5-carboxylate 
• 141872-09-5 ethyl 2-methyl-4-{N-butyl-N-[(2'-[N-triphenylmethyl-1H-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyrimidine-5-carboxylate 
• 1135957-83-3 2-(benzoylmethylene)-7-methyl-2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-one 
• 1135957-82-2 7-amino-8-benzoyl-2-methylpyrido[4,3-d]pyrimidin-5(6H)-one 
• 189745-28-6 5-(chloromethyl)-2-methyl-pyrimidin-4-amine 
• 89640-71-1 2-methyl-6-thioxo-1,6-dihydro-pyrimidine-5-carboxylic acid 
• 698-29-3 2-methyl-4-amino-5-cyanopyrimidine 
• 141871-80-9 2-Methyl-4-{pentyl-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-pyrimidine-5-carboxylic acid ethyl ester 
• 141871-64-9 4-{(2-Methoxy-ethyl)-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-2-methyl-pyrimidine-5-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Structure-based design of a new series of N-(piperidin-3-yl)pyrimidine-5-carboxamides as renin inhibitors

The action of the aspartyl protease renin is the rate-limiting initial step of the renin-angiotensin-aldosterone system. Therefore, renin is a particularly promising target for blood pressure as well as onset and progression of cardiovascular and renal diseases. New pyrimidine derivatives 5–14 were designed in an attempt to enhance the renin inhibitory activity of compound 3 identified by our previous fragment-based drug design approach. Introduction of a basic amine essential for interaction with the two aspartic acids in the catalytic site and optimization of the S1/S3 binding elements including an induced-fit structural change of Leu114 (‘Leu-in’ to ‘Leu-out’) by a rational structure-based drug design approach led to the discovery of N-(piperidin-3-yl)pyrimidine-5-carboxamide 14, a 65,000-fold more potent renin inhibitor than compound 3. Surprisingly, this remarkable enhancement in the inhibitory activity of compound 14 has been achieved by the overall addition of only seven heavy atoms to compound 3. Compound 14 demonstrated excellent selectivity over other aspartyl proteases and moderate oral bioavailability in rats.

Optimisation of pharmacokinetic properties in a neutral series of 11β-HSD1 inhibitors

11β-HSD1 is increasingly seen as an attractive target for the treatment of type II diabetes and other elements of the metabolic syndrome. In this program of work we describe how a series of neutral 2-thioalkyl-pyridine 11β-HSD1 inhibitors were optimized in terms of their pharmacokinetic properties to give compounds with excellent bioavailability in both rat and dog through a core change to pyrimidine. A potential reactive metabolite issue with 4-thioalkyl-pyrimidines was circumvented by a switch from sulfur to carbon substitution.

SUBSTITUTED PYRIMIDIN-5-CARBOXAMIDES 281

A compound of formula (I): and pharmaceutically-acceptable salts thereof wherein the variable groups are defined within; their use in the inhibition of 11betaHSD1, processes for making them and pharmaceutical compositions comprising them are also described.

Novel inhibitors of AP-1 and NF-κB mediated gene expression: Structure-activity relationship studies of ethyl 4-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-2-(trifluoromethyl)pyrimidine-5-carb oxylate

In an effort to identify novel inhibitors of AP-1 and NF-κB mediated transcriptional activation, several analogues of ethyl 4-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-2-(trifluoromethyl)pyrimidine-5-carb oxylate (1) were synthesized and tested in two in vitro assays. The 2-(2'-thienyl) substituted compound (11) was identified as the most potent in this series. (C) 2000 Elsevier Science Ltd. All rights reserved.