7193-87-5

Basic information

• Product Name: 2,4-DIETHOXY-5-METHYLPYRIMIDINE
• Synonyms: 2,4-DIETHOXY-5-METHYLPYRIMIDINE;Einecs 230-558-2;Pyrimidine, 2,4-diethoxy-5-methyl-
• CAS NO: 7193-87-5
• Molecular Formula: C₉H₁₄N₂O₂
• Molecular Weight: 182.22
• EINECS: 230-558-2
• Mol File: 7193-87-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 283.7 °C at 760 mmHg
• Flash Point: 104.1 °C
• Appearance: /
• Density: 1.052 g/cm³
• Vapor Pressure: 0.00532mmHg at 25°C
• Refractive Index: 1.487
• CAS DataBase Reference: 2,4-DIETHOXY-5-METHYLPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIETHOXY-5-METHYLPYRIMIDINE(7193-87-5)
• EPA Substance Registry System: 2,4-DIETHOXY-5-METHYLPYRIMIDINE(7193-87-5)

Safety Data

• Hazardous Substances Data: 7193-87-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 22, p. 2927, 1992 DOI: 10.1080/00397919208021116

InChI:InChI=1/C9H14N2O2/c1-4-12-8-7(3)6-10-9(11-8)13-5-2/h6H,4-5H2,1-3H3

Upstream product

• 114536-12-8 2-ethanesulfonyl-4-ethoxy-5-methyl-pyrimidine 
• 141-52-6 sodium ethanolate 
• 1780-31-0 2,6-dichloro-5-methylpyrimidine 
• 64-17-5 ethanol 
• 99516-33-3 4-ethoxy-2-ethylsulfanyl-5-methyl-pyrimidine 
• 13480-95-0 2-ethylthio-3,4-dihydro-5-methylpyrimidin-4-one 
• 13480-96-1 4-chloro-2-ethylsulfanyl-5-methyl-pyrimidine 
• 65-71-4 thymin 
• 64-67-5 diethyl sulfate 
• 98546-80-6 2-ethanesulfonyl-4-chloro-5-methyl-pyrimidine 

Downstream Products

• 3180-78-7 1-(β-D-glucopyranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione 
• 25307-94-2 1,5-dimethyl-4-methylamino-1H-pyrimidin-2-one 
• 3258-09-1 α-thymidine 
• 2140-61-6 4-amino-5-methyl-1-α-D-ribofuranosyl-1H-pyrimidin-2-one 
• 6220-45-7 4-ethoxy-1,5-dimethyl-1H-pyrimidin-2-one 

Relevant articles and documents

Structurally Simple, Readily Available Peptidomimetic 1-Benzyl-5-methyl-4-(n-octylamino)pyrimidin-2(1 H)-one Exhibited Efficient Cardioprotection in a Myocardial Ischemia (MI) Mouse Model

TLR4, a member of the Toll-like receptor (TLR) family, serves as a pattern recognition receptor in the innate immune response to microbial pathogens. TLR4 also regulates the inflammatory reaction to ischemic injury in the heart. The TRIF-related adaptor molecule (TRAM) is an adapter that recruits the Toll/interleukin 1 receptor (TIR) domain, which contains adapter-inducing IFN-β (TRIF), to activate TLR4, following TRIF-dependent cytokine gene transcription. On the basis of a known TRAM-derived decoy peptide, 10 of its peptidomimetics were synthesized. One of them, 1-benzyl-5-methyl-4-(n-octylamino)pyrimidin-2(1H)-one (21), exhibited high potency and efficacy in vitro. In vitro results and in silico analysis provided evidence for the possible direct interaction of 21 with the TLR4 complex. Administered in mice, 21 was able to block the pathophysiological manifestation of MI, restoring the concomitant tissue damage, with a 100% survival rate. Thus, inhibition of TLR4-mediated inflammation in postischemic myocardium could be used as an approach for developing cardioprotective drugs.

HSAB-driven chemoselective N1-alkylation of pyrimidine bases and their 4-methoxy- or 4-acetylamino-derivatives

The lithium salts of the conjugated bases of 4-methoxy- and 4-acetylamino-2(1H)-pyrimidinones 1-3 undergo highly chemoselective N1-methylation or ethylation when treated with methyl- or ethylsulfate (hard electrophiles) in dry dioxane, while the use of DMF as solvent results in competitive O2-alkylation. Potassium salts of the same bases in DMF undergo prevalent O2-attack. Under the same conditions, a similar but less chemoselective behaviour is observed in alkylation of thymine and uracil, where some N3-attack occurs. This can be rationalised in terms of the HSAB principle.