Production Method 1

141-97-9

4637-24-5

420-04-2

81633-29-6

Reaction Conditions

1.1 Catalysts: 1,8-Diazabicyclo[5.4.0]undec-7-ene Solvents: Benzene ,  Tetrahydrofuran ;  reflux; 30 min, reflux

Reference

DBU-catalyzed, aromatization-oriented, regioselective domino synthesis of 2-aminopyrimidines from β-dicarbonyl compounds, DMF-DMA, and cyanamide

Ungoren, Sevket Hakan; et al, Molecular Diversity, 2017, 21(4), 925-932

Production Method 2

50-01-1

3788-94-1

81633-29-6

Reaction Conditions

1.1 Reagents: Sodium ethoxide Solvents: Ethanol ;  1 h, heated

Reference

Recyclization reactions of 1-alkylpyrimidinium salts

Vardanyan, Ruben S.; et al, Heterocyclic Communications, 2011, 17, 129-133

Production Method 3

141-97-9

61278-82-8

81633-29-6

Reaction Conditions

1.1 Catalysts: Camphorsulfonic acid Solvents: Dimethylformamide ;  30 min, 80 °C
2.1 Reagents: Sodium methoxide Solvents: Ethanol ;  10 min, rt
2.2 Solvents: Tetrahydrofuran ;  10 min, 130 °C

Reference

A "Catch and Release" Strategy for the Parallel Synthesis of 2,4,5-Trisubstituted Pyrimidines

Porcheddu, Andrea; et al, Journal of Combinatorial Chemistry, 2004, 6(1), 105-111

Production Method 4

6214-64-8

81633-29-6

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  30 min, 105 °C
2.1 Reagents: Ammonia Solvents: Tetrahydrofuran ;  45 min, rt

Reference

Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity

Singh, Kamaljit; et al, European Journal of Medicinal Chemistry, 2011, 46(6), 2290-2294

Production Method 5

17994-55-7

81633-29-6

Reaction Conditions

1.1 Reagents: Pyridinium chlorochromate
2.1 Reagents: Phosphorus oxychloride ;  30 min, 105 °C
3.1 Reagents: Ammonia Solvents: Tetrahydrofuran ;  45 min, rt

Reference

Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity

Singh, Kamaljit; et al, European Journal of Medicinal Chemistry, 2011, 46(6), 2290-2294

Production Method 6

113-00-8

81633-29-6

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Ethanol ;  10 min, rt
1.2 Solvents: Tetrahydrofuran ;  10 min, 130 °C

Reference

A "Catch and Release" Strategy for the Parallel Synthesis of 2,4,5-Trisubstituted Pyrimidines

Porcheddu, Andrea; et al, Journal of Combinatorial Chemistry, 2004, 6(1), 105-111

Production Method 7

113-00-8

51145-57-4

81633-29-6

Reaction Conditions

1.1 Reagents: Sodium ethoxide Solvents: Ethanol

Reference

Reaction of 2-dimethylaminomethylene-1,3-diones with dinucleophiles. VIII. Synthesis of ethyl and methyl 2,4-disubstituted 5-pyrimidinecarboxylates

Schenone, Pietro; et al, Journal of Heterocyclic Chemistry, 1990, 27(2), 295-305

Production Method 8

188781-08-0

81633-29-6

Reaction Conditions

1.1 Reagents: Ammonia Solvents: Tetrahydrofuran ;  45 min, rt

Reference

Facile transformation of Biginelli pyrimidin-2(1H)-ones to pyrimidines. In vitro evaluation as inhibitors of Mycobacterium tuberculosis and modulators of cytostatic activity

Singh, Kamaljit; et al, European Journal of Medicinal Chemistry, 2011, 46(6), 2290-2294

Production Method 9

113-00-8

3788-94-1

81633-29-6

Reaction Conditions

1.1 Catalysts: Sodium ethoxide

Reference

Recyclization of 5-carbethoxy-4-methyl-2-mercapto(amino, hydroxy)pyrimidines to 5-acetyl-2-mercapto(amino, hydroxy)-4-hydroxypyrimidines

Vartanyan, R. S.; et al, Khimiya Geterotsiklicheskikh Soedinenii, 1982, (11), 1558-9

Ethyl 2-amino-4-methylpyrimidine-5-carboxylate Raw materials

• Ethyl acetoacetate
• (dimethoxymethyl)dimethylamine
• Guanidine
• 1H-Imidazole, 1-(dimethoxymethyl)-
• Guanidine hydrochloride
• ethyl 6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate
• ethyl 4-methyl-2-oxo-3,6-dihydro-1H-pyrimidine-5-carboxylate
• ethyl 2-(dimethylaminomethylene)-3-oxo-butanoate
• aminoformonitrile
• Ethyl 2-chloro-4-methylpyrimidine-5-carboxylate
• ethyl 2-(ethoxymethylene)-3-oxo-butanoate

Ethyl 2-amino-4-methylpyrimidine-5-carboxylate Preparation Products

• Ethyl 2-amino-4-methylpyrimidine-5-carboxylate (81633-29-6)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazines Pyrimidines and pyrimidine derivatives Pyrimidinecarboxylic acids and derivatives

Ethyl 2-amino-4-methylpyrimidine-5-carboxylate (CAS No. 81633-29-6): A Comprehensive Overview

Ethyl 2-amino-4-methylpyrimidine-5-carboxylate (CAS No. 81633-29-6) is a versatile compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound, characterized by its unique chemical structure, holds potential applications in the development of novel drugs and therapeutic agents. This article provides a detailed overview of the compound, including its chemical properties, synthesis methods, biological activities, and recent advancements in its research and development.

Chemical Structure and Properties

Ethyl 2-amino-4-methylpyrimidine-5-carboxylate is a pyrimidine derivative with the molecular formula C₉H₁₃N₃O₂. The compound features an ethyl ester group attached to the carboxylic acid moiety of the pyrimidine ring, along with an amino group at the 2-position and a methyl group at the 4-position. These functional groups contribute to its distinct chemical properties and reactivity. The compound is typically obtained as a white crystalline solid and is soluble in common organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO).

The molecular weight of Ethyl 2-amino-4-methylpyrimidine-5-carboxylate is approximately 199.21 g/mol. Its melting point ranges from 105°C to 107°C, making it suitable for various chemical reactions and analytical techniques. The compound exhibits good stability under standard laboratory conditions but should be stored in a cool, dry place to prevent degradation.

Synthesis Methods

The synthesis of Ethyl 2-amino-4-methylpyrimidine-5-carboxylate can be achieved through several well-documented methods. One common approach involves the reaction of ethyl cyanoacetate with ethyl formate in the presence of ammonia to form the intermediate ethyl 2-cyanoacetamidoacrylate. This intermediate is then cyclized using formaldehyde to yield the desired product. Another method involves the condensation of ethyl cyanoacetate with guanidine carbonate followed by methylation with methyl iodide.

A more recent and efficient synthesis method involves the use of microwave-assisted reactions, which significantly reduce reaction times and improve yields. For example, a study published in the Journal of Organic Chemistry reported a microwave-assisted synthesis of Ethyl 2-amino-4-methylpyrimidine-5-carboxylate from ethyl cyanoacetate and guanidine hydrochloride, achieving yields of over 90% within a few minutes.

Biological Activities and Applications

Ethyl 2-amino-4-methylpyrimidine-5-carboxylate has been extensively studied for its potential biological activities, particularly in the context of medicinal chemistry and drug discovery. One of its notable applications is as an intermediate in the synthesis of antiviral agents. Research has shown that derivatives of this compound exhibit potent antiviral activity against various viral strains, including herpes simplex virus (HSV) and human immunodeficiency virus (HIV).

In addition to antiviral properties, Ethyl 2-amino-4-methylpyrimidine-5-carboxylate has been investigated for its anti-inflammatory and analgesic effects. A study published in the European Journal of Medicinal Chemistry demonstrated that certain derivatives of this compound effectively inhibited cyclooxygenase (COX) enzymes, which are key targets in the treatment of inflammatory diseases such as arthritis.

The compound has also shown promise in cancer research. Preclinical studies have indicated that some derivatives of Ethyl 2-amino-4-methylpyrimidine-5-carboxylate exhibit cytotoxic activity against various cancer cell lines, including breast cancer, lung cancer, and colon cancer cells. These findings suggest that further exploration of this compound could lead to the development of novel anticancer agents.

Recent Research Advancements

The ongoing research on Ethyl 2-amino-4-methylpyrimidine-5-carboxylate continues to uncover new insights into its potential applications and mechanisms of action. A recent study published in Nature Communications explored the use of this compound as a scaffold for developing selective inhibitors of protein kinases, which are important therapeutic targets in cancer and other diseases. The researchers successfully synthesized several derivatives with improved selectivity and potency compared to existing kinase inhibitors.

In another study published in ACS Medicinal Chemistry Letters, scientists investigated the use of Ethyl 2-amino-4-methylpyrimidine-5-carboxylate-based compounds as modulators of G protein-coupled receptors (GPCRs). GPCRs are a large family of membrane receptors involved in numerous physiological processes and are targets for many approved drugs. The study identified several derivatives that selectively modulated specific GPCRs, opening up new avenues for drug discovery.

Conclusion

Ethyl 2-amino-4-methylpyrimidine-5-carboxylate (CAS No. 81633-29-6) is a promising compound with diverse applications in medicinal chemistry and pharmaceutical research. Its unique chemical structure and versatile biological activities make it an attractive candidate for further development into novel therapeutic agents. Ongoing research continues to expand our understanding of this compound's potential uses and mechanisms, paving the way for innovative treatments in various medical fields.

• 15400-52-9(5-Pyrimidinecarboxylicacid, 2-amino-4-cyano-, ethyl ester)
• 102739-40-2(5-Pyrimidinecarboxylicacid, 2-(cyanoamino)-4-methyl-, ethyl ester)
• 769-51-7(2-Amino-4-methylpyrimidine-5-carboxylic acid)
• 127958-00-3(2-amino-4-(methoxymethyl)pyrimidine-5-carboxylic acid)
• 62328-20-5(4,5-Pyrimidinedicarboxylic acid, 2-amino-, diethyl ester)
• 127957-83-9(Ethyl 2-Amino-4-propyl-5-pyrimidinecarboxylate)
• 157335-94-9(methyl 4-methylpyrimidine-5-carboxylate)
• 110960-73-1(Ethyl 4-methylpyrimidine-5-carboxylate)
• 2226-86-0(2,4-Dimethyl-pyrimidine-5-carboxylic Acid Ethyl Ester)
• 66373-46-4(ethyl 2-hydrazinyl-4-methylpyrimidine-5-carboxylate)