15400-53-0

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique molecular structure allows it to be a key component in the development of new drugs, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
In the field of chemical research, 2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE serves as a valuable compound for studying the properties and reactivity of aminopyrimidine derivatives. Its ethoxycarbonyl group can be further modified or used as a starting point for the synthesis of more complex molecules with potential applications in various industries.
Used in Material Science:
The unique structure of 2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE also makes it a candidate for the development of new materials with specific properties. Its potential use in material science could include the creation of novel polymers, coatings, or other materials with tailored characteristics for various applications.
Used in Agricultural Chemistry:
2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE may also find applications in agricultural chemistry, where it could be used as a building block for the development of new pesticides, herbicides, or other agrochemicals. Its unique structure and functional groups could provide new modes of action or improved efficacy in controlling pests and diseases in agriculture.

InChI:InChI=1/C7H9N3O3/c1-2-13-6(12)4-3-9-7(8)10-5(4)11/h3H,2H2,1H3,(H3,8,9,10,11)

Upstream product

• 593-85-1 diguanidine carbonate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 124-46-9 guanidine hydrogen carbonate 
• 113-00-8 guanidine nitrate 

Downstream Products

• 229484-39-3 ethyl 5,8-dihydro-3-methyl-5-oxo-8-(1-oxo-1-phenylpropan-2-yl)-2-phenylimidazo[1,2-a]pyrimidine-6-carboxylate 
• 484691-31-8 5-hydroxy-2-(4-methoxy-phenyl)-imidazo[1,2-a]pyrimidine-6-carboxylic acid ethyl ester 
• 84332-39-8 2-Amino-4-ethoxy-pyrimidine-5-carboxylic acid ((R)-1-ethyl-pyrrolidin-2-ylmethyl)-amide 
• 72429-48-2 2-amino-4-methoxy-pyrimidine-5-carboxylic acid 1-propyl-pyrrolidin-2-ylmethyl-amide 
• 84332-12-7 2-amino-4-methoxy-pyrimidine-5-carboxylic acid 1-methyl-pyrrolidin-2-ylmethyl-amide 
• 484691-37-4 2-(4-butyrylamino-phenyl)-8-(2-fluoro-benzyl)-5-oxo-5,8-dihydro-imidazo[1,2-a]pyrimidine-6-carboxylic acid 1-ethyl-propyl ester 
• 484691-36-3 2-(4-butyrylamino-phenyl)-8-(2-fluoro-benzyl)-5-oxo-5,8-dihydro-imidazo[1,2-a]pyrimidine-6-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Critical modification to bulk scale synthesis of 2-amino-5-carboethoxy-4-hydroxypyrimidine

Pyrimidines and pyridines are choice for modern day medicinal chemistry. Pyrimidine synthons are synthesized form guanidine and different substituted malonates. One of such pyrimidine ring synthon is 2-amino-5-carboethoxy-4-hydroxy pyrimidine. The commercially deployed synthesis involved a mixture of KOH and guanidine carbonate and gradual temperature controlled addition of diethylethoxy methylene melonate giving a yellow precipitate. The precipitate is cooled to around 5 °C and recrystallized from ethanol-water mixture. Though purity is never an issue in this popular process, yields are very low (70-75 %). The GC analysis of reaction mixture indicated that almost starting material was left unreacted and the first yellow precipitate formation is the rate determining step. We report silica functionalized magnetic particles as material support for synthesis of 2-amino-5carboethoxy-4-hydroxy pyrimidine. The cyclization reaction yields are reported to be enhanced due to presence of “near-homogeneous” nanomaterial catalyst. The prominent catalyst of interest to us is Fe3O4@SiO2 of 40 nm size. The particles are produced by modified Stober process giving consistent yields and coating of SiO2. The structural characterization is performed with SEM, TEM, IR and the data are consistent across multiple batches. The use of 40 nm size Fe3O4@SiO2 enabled higher yields of cyclization step in synthesis of 2-amino-5-carboethoxy-4-hydroxy pyrimidine. The mechanism of catalysis is stabilization of hetero atoms on the acidic silica surface and hence formation of pyrimidine. The study with different sized nanoparticles has indicated 40 nm size seems to be optimum and ability of catalysis is reduced as the size of nanoparticles has increased. The reaction performed at different batch sizes has indicated that 5 % (w/v) catalyst is optimal in the reaction. This process modification has far reaching applications in medicinal chemistry and bulk drug synthesis.

2-(2-substituted-4-hydroxypyrimidinyl-5-carboxamido)acetic acid compound, and preparation method and application thereof

The invention discloses a 2-(2-substituted-4-hydroxypyrimidinyl-5-carboxamido)acetic acid compound with a structure shown as a formula I and a pharmaceutically acceptable salt thereof. The invention also discloses a preparation method of the compound. The invention further discloses pharmaceutical compositions taking the compound shown as the formula I or the pharmaceutically acceptable salt thereof as an active ingredient, and application of the pharmaceutical compositions as a PHD inhibitor in treatment of anemia caused by erythropoietin decrease or deficiency, especially in treatment of renal anemia.

Synthesis and evaluation of homo-bivalent GnRHR ligands

G protein coupled receptors (GPCRs) are important drug targets in pharmaceutical research. Traditionally, most research efforts have been devoted towards the design of small molecule agonists and antagonists. An interesting, yet poorly investigated class of GPCR modulators comprise the bivalent ligands, in which two receptor pharmacophores are incorporated. Here, we set out to develop a general strategy for the synthesis of bivalent compounds that are projected to bind to the human gonadotropin-releasing hormone receptor (GnRHR). Our results on the dimerisation of a known GnRHR antagonist, with as key step the Huisgen 1,3-cycloaddition, and their ability to bind to and antagonize GnRH-induced GnRHR stimulation, are presented here.

Nitrogen-containing heterocyclic compounds, their production and use

A compound of the formula: wherein one of A and D is N and the other is C, or both are N; B is N or C; m is 0-3; R1, R2 and R3 each is (i) H or (ii) a group bound via C, N, O or S; R4 is a group bound via C; R5 is H or a group bound via C or O; R6 is H or a group bound via C; R7 is a homo- or hetero-cyclic group which may be substituted; or a salt thereof possesses excellent gonadotropin-releasing hormone antagonizing activity, and is useful as a prophylactic or therapeutic agent for sex hormone-dependent diseases, and so forth.