31167-05-2

Basic information

• Product Name: 2,4-Bis(trimethylsiloxy)-5-ethylpyrimidine
• Synonyms: 2,4-Bis(trimethylsiloxy)-5-ethylpyrimidine;Pyrimidine, 5-ethyl-2,4-bis[(trimethylsilyl)oxy]-;2,4-Bis(trimethylsilyl)-5-ethyluracil;5-Ethyl-2,4-bis[(trimethylsilyl)oxy]pyrimidine;2,4-Bis[(trimethylsilyl)oxy]-5-ethylpyrimidine
• CAS NO: 31167-05-2
• Molecular Formula: C₁₂H₂₄N₂O₂Si₂
• Molecular Weight: 284.5
• Mol File: 31167-05-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 304.3°C at 760 mmHg
• Flash Point: 137.8°C
• Appearance: /
• Density: 0.967g/cm³
• Vapor Pressure: 0.00159mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: 2,4-Bis(trimethylsiloxy)-5-ethylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Bis(trimethylsiloxy)-5-ethylpyrimidine(31167-05-2)
• EPA Substance Registry System: 2,4-Bis(trimethylsiloxy)-5-ethylpyrimidine(31167-05-2)

Safety Data

• Hazardous Substances Data: 31167-05-2(Hazardous Substances Data)

Usage

Chemical Properties

Colourless oil, very sensitive to moisture

InChI:InChI=1/C12H24N2O2Si2/c1-8-10-9-13-12(16-18(5,6)7)14-11(10)15-17(2,3)4/h9H,8H2,1-7H3

Upstream product

• 4212-49-1 5-ethyluracil 
• 75-77-4 chloro-trimethyl-silane 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 10416-59-8 N,O-Bis(trimethylsilyl)acetamide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 191794-45-3 1-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-ethyl-1H-pyrimidine-2,4-dione 
• 155831-60-0 5-ethyl-1-<<(1'-phenyl-2'-hydroxy)ethoxy>methyl>uracil 
• 155831-63-3 5-ethyl-1-<<1'-phenyl-2'-(t-butyldimethylsilyloxy)ethoxy>methyl>uracil 
• 155831-66-6 5-ethyl-1-<<1'-phenyl-2'(t-butyldimethylsilyloxy)ethoxy>methyl>-6-(phenylthio)uracil 
• 155831-70-2 5-ethyl-1-<<1'-phenyl-2'-(t-butyldimethylsilyloxy)ethoxy>methyl>-6-(phenylseleno)uracil 
• 78103-19-2 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-ribofuranosyl)-4-trimethylsilyloxy-5-ethyl-2,4(1H,3H)-pyrimidinedione 
• 29900-44-5 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-5-ethyl-2,4(1H,3H)-pyrimidinedione 
• 957470-77-8 C₂₅H₂₃⁽¹⁸⁾FN₂O₇ 

Relevant articles and documents

A novel synthesis of 4'-thionucleosides and a potential stereospecific route to pyrimidine nucleosides

Starting with the L-ascorbate derived epoxide 1, a di-t-butyl dithioacetal cyclisation route to 2'-deoxy-4'-thionucleosides has been developed. Based on an intermediate in this route, a novel and stereospecific route to α- or β-pyrimidine nucleosides has been conceived, but its implementation failed at a key ring-closure step. (C) 2000 Elsevier Science Ltd.

Synthesis and antiviral activities of 5-substituted 1-(2-deoxy-2-c- methylene-4-thio-β-d-ertythropentofuranosyl)uracils

Various 5-substituted 1-(2-deoxy-2-C-methylene-4-thio-β-D- erythropentofuranosyl)uracils (4'-thioDMDUs) were synthesized from D-glucose via sila-Pummerer-type glycosylation. All of the β-anomers of 5-substituted 4'-thioDMDU, except the 5-hydroxyethyl derivative, showed potent anti-HSV-1 activity (ED50 = 0.016-0.096 μg/mL). 5-Ethyl- and 5-iodo-4'-thioDMDUs were also active against HSV-2 (ED50 = 0.17 and 0.86 μg/mL, respectively). 5- Bromovinyl-4'-thioDMDU was particularly active against VZV (ED50 = 0.013 μg/mL).

A convenient one-pot synthesis of acyclonucleosides

Bis(trimethylsilyl)pyrimidine bases were treated directly with 1,3-dioxolane (or 2-methyl-1,3-dioxolane), chlorotrimethylsilane and a metal iodide, such as KI or NaI, in acetonitrile at room temperature to afford acyclopyrimidine derivatives, including 2-thiopyrimidine derivatives, in good yields. Introduction of an acyclic chain into 2-thiopyrimidine bases, however, necessitated the use of 2 eq of the reagents.