57401-76-0

Basic information

• Product Name: 2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: ETHYL 2-AMINO-5-PYRIMIDINECARBOXYLATE;2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER;5-Carbethoxy-2-pyriMidinaMine;5-PyriMidinecarboxylic acid, 2-aMino-, ethyl ester;2-Amino-5-pyrimidinecarboxylic acid ethyl ester;NSC 165511;EOS-60351
• CAS NO: 57401-76-0
• Molecular Formula: C₇H₉N₃O₂
• Molecular Weight: 167.17
• Product Categories: pharmacetical;API intermediates;Heterocycle-Pyrimidine series
• Mol File: 57401-76-0.mol

Chemical Properties

• Melting Point: 147-149℃
• Boiling Point: 349℃
• Flash Point: 165℃
• Appearance: /
• Density: 1.261
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.94±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER(57401-76-0)
• EPA Substance Registry System: 2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER(57401-76-0)

Safety Data

• Hazardous Substances Data: 57401-76-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER is used as a synthetic reagent for the production of retinoidal pyrimidinecarboxylic acids. These compounds are of significant interest due to their potential applications in the development of novel therapeutic agents, particularly in the treatment of various diseases and conditions. The ester's role in the synthesis process is to facilitate the formation of the desired retinoidal pyrimidinecarboxylic acid molecules, which can then be further studied and potentially utilized in the creation of new medications.
Used in Chemical Research:
In addition to its applications in the pharmaceutical industry, 2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER is also used as a research tool in the field of chemistry. Its unique properties make it a valuable compound for studying various chemical reactions and mechanisms, as well as for exploring the potential of new synthetic pathways. By understanding the behavior of this ester in different chemical contexts, researchers can gain insights into the broader principles of organic chemistry and potentially discover new methods for synthesizing other complex molecules.

InChI:InChI=1/C6H7N3O2/c1-11-5(10)4-2-8-6(7)9-3-4/h2-3H,1H3,(H2,7,8,9)

Upstream product

• 89793-12-4 ethyl 2-chloropyrimidine-5-carboxylate 
• 97430-37-0 2-(ethoxycarbonyl)-3-hydroxyacrolein 
• 593-87-3 guanidine acetic acid 
• 95928-49-7 ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate 
• 763-69-9 ethyl 3-ethoxypropionate 
• 2974-30-3 (Z)-ethyl-2-(ethoxymethyl)-3-methoxyacrylate 
• 33458-27-4 ethyl 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 151323-66-9 ethyl 2-(ethylthio)pyrimidine-5-carboxylate 
• 5909-24-0 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester 
• 73781-88-1 ethyl 2-(methylthio)pyrimidine-5-carboxylate 
• 148550-51-0 ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate 
• 506-93-4 guanidine nitrate 
• 97-63-2 methyl methacrylate 
• 2223-96-3 4-chloro-2-ethylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester 

Downstream Products

• 3167-50-8 2-amino-pyrimidine-5-carboxylic acid 
• 1428848-62-7 (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(2-(methylsulfonamido)pyrimidine-5-carbonyloxy)acetoxy)ethyl)pyridine 1-oxide 

Relevant articles and documents

Simple preparation method of 2-aminopyrimidine-5-formate

The invention provides a simple preparation method of 2-aminopyrimidine-5-formate. The preparation method comprises: carrying out a substitution reaction on 2-methacrylate as a raw material and a halogenating reagent 1, carrying out an addition reaction with a halogenating reagent 2 to obtain 2,3,3-trihalogenated-2-halogenated methyl propionate, and condensing the obtained 2,3,3-trihalogenated-2-halogenated methyl propionate and a guanidine salt to prepare 2-aminopyrimidine-5-formate. According to the invention, the raw materials used in the method are cheap, easy to obtain and low in cost; and the preparation method has characteristics of simpleness, easily achieved conditions, good operation safety, little wastewater generation, environmental protection, high target product yield and high target product purity, and is suitable for industrial production.

Highly efficient one-pot amination of carboxylate-substituted nitrogen-containing heteroaryl chlorides via Staudinger reaction

An efficient one-pot method for the synthesis of tert-butyl 6-aminonicotinate (5) is described. The key transformation involves displacement of the chloro group in tert-butyl 6-chloronicotinate (2) with azide followed by a Staudinger reaction. The scope of this methodology is further extended for the synthesis of a series of carboxylate-substituted heteroaryl amines. In particular, we synthesized tert-butyl carboxylate-substituted amino-pyridine, -pyridazine, and -pyrazine. In addition to one-pot conversion, short reaction time, simplicity of operation, ease of purification, and good yields are the key advantages of this methodology.

DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS

The invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to compounds that are derivatives of 1-phenyl-2-pyridinyl alkyl alcohols, methods of preparing such compounds, compositions containing them and therapeutic use thereof.

DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS

The invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to compounds that are derivatives of 1-phenyl-2-pyridinyl alkyl alcohols, methods of preparing such compounds, compositions containing them and therapeutic use thereof.

Retinoidal pyrimidinecarboxylic acids. Unexpected diaza-substituent effects in retinobenzoic acids

Several pyridine- and pyrimidine-carboxylic acids were synthesized as ligand candidates for retinoid nuclear receptors, retinoic acid receptors (RARs) and retinoic X receptors (RXRs). Although the pyridine derivatives, 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]pyridine- 3-carboxylic acid (2b) and 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]pyridin e-3-carboxylic acid (5b) are more potent than the corresponding benzoic acid-type retinoids, Am80 (2a) and Am580 (5a), the replacement of the benzene ring of Am580 (5a), Am555 (6a), or Am55 (7a) with a pyrimidine ring caused loss of the retinoidal activity both in HL-60 cell differentiation assay and in RAR transactivation assay using COS-1 cells. On the other hand, pyrimidine analogs (PA series, 10 and 11) of potent RXR agonists (retinoid synergists) with a diphenylamine skeleton (DA series, 8 and 9) exhibited potent retinoid synergistic activity in HL-60 cell differentiation assay and activated RXRs. Among the synthesized compounds, 2-[N-n-propyl-N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino] pyrimidine-5-carboxylic acid (PA013, 10e) is most active retinoid synergist in HL-60 assay.

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles. VIII. Synthesis of Ethyl and Methyl 2,4-Disubstituted 5-Pyrimidinecarboxylates

Reaction of ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates with N-C-N dinucleophiles such as guanidine, acetamidine or benzamidine afforded in high yields the relative esters of 4-substituted 2-amino-, 2-methyl- or 2-phenyl-5-pyrimidinecarboxylic acids, respectively.These esters were hydrolyzed to the corresponding carboxylic acids, which were converted by heating to 4-substituted 2-pyrimidinamines, 2-methyl or 2-phenylpyrimidines, respectively, generally in excellent yields.The 4-unsubstituted ethyl 2-amino-, 2-methyl- and 2-phenyl-5-pyrimidinecarboxylateswere obtained in moderate yields by reaction of the above dinucleophiles with ethyl 2,2-diformylacetate.These esters were hydrolyzed and the corresponding acids (with the exception of the 2-methyl derivative) were decarboxylated to give 2-pyrimidinamine and 2-phenylpyrimidine in satisfactory yields.