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

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

Downstream Products

• 29900-44-5 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-5-ethyl-2,4(1H,3H)-pyrimidinedione 
• 29900-45-6 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-ribofuranosyl)-5-ethyl-2,4(1H,3H)-pyrimidinedione 
• 87782-41-0 Benzoic acid (2R,3R,4S,5R)-3-acetoxy-5-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-tetrahydro-furan-2-ylmethyl ester 
• 95740-18-4 1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranofuranosyl)-5-ethyluracil 
• 106835-91-0 C₂₅H₂₃FN₂O₇ 
• 84017-59-4 2',5'-di-O-p-chlorobenzoyl-5'-ethyl-3'-deoxyuridine 
• 172473-13-1 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)-5-ethyluracil 
• 191794-45-3 1-((3S,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-ethyl-1H-pyrimidine-2,4-dione 

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.

5-Substituted UTP derivatives as P2Y2 receptor agonists

A series of 5-alkyl-substituted UTP derivatives, which had been synthesized previously with a moderate degree of purity, was resynthesized, purified, and characterized. Synthetic and purification procedures were optimized. New spectroscopic data, including 13C- and 31P NMR data, are presented. Phosphorylation reactions yielded a number of side products, such as the 2'-, 3'-, and 5'-monophosphates, the 2',3'-cyclic monophosphates, and the 2',3'-cyclic phosphates of the 5'-triphosphates. Furthermore, raw products were contaminated with inorganic phosphates, including cyclometatriphosphate, phosphate, and pyrophosphate. The uracil nucleotides were investigated for their potency to increase intracellular calcium concentrations by stimulation of P2Y2 receptors (P2Y2R) on NG108- 15 cells, a mouse neuroblastoma x glioma cell line, and in human basal epithelial airway cells, including a cystic fibrosis (CF/T43) cell line. UTP exhibited EC50 values of ca. 1 μM (in NG108-15 cells) and of 0.1 μM (in CF/T43 cells), respectively. 5-Substituted UTP derivatives were agonists at the P2Y2R, but were less potent than UTP. 5-Ethyl-UTP, for example, exhibited an EC50 value of 99 μM at P2Y2R of NG108-15 cells and proved to be a full agonist. With increasing volume of the 5- substituent of UTP derivatives, P2Y2 activity decreased.

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 facile, alternative synthesis of 4'-thioarabinonucleosides and their biological activities

4'-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from D-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pummerer rearrangement after protection of the hy

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.

β-Anomer selectivity in 2′-deoxynucleoside synthesis: A novel approach using an acyl carbamate directing group

Glycosylation of silylated pyrimidines using a phenyl 2-deoxy-3-O-(N-benzoyl)carbamoyl-1-thio-D-erythro-pentofuranoside yielded 2-deoxy-β-ribonucleosides in good yields with excellent anomeric selectivity. This prototype 3-O-carbamate directing group was readily formed and removed in high yields.

6-pyridyl substituted pyrimidine derivatives

Novel 6-pyridyl substituted pyrimidine derivatives are disclosed for use as antiviral agents, particularly for the treatment of retroviral infections such as HIV infections and related disorders, as well as for use in anti-cancer therapies to improve the efficacy of anti-cancer therapeutics. These compounds and their pharmacologically acceptable salts operate to disrupt viral replication an exhibit lower cell toxicity, thereby providing more efficient agents for use alone or in conjunction with other chemical or biological agents to provide prolonged antiviral therapy. In addition, the compounds can be used to increase the efficacy of anti-cancer therapeutics including 5-fluropyrimidines such as 5-fluorouracil, thereby reducing the dosage requirement of the therapeutic in anti-cancer therapies so as to decrease toxic effects to the host.

Synthesis and anti-HIV-1 activities of 6-arylthio and 6- arylselenoacyclonucleosides

6-Arylthio and 6-arylselenoacyclonucleosides was synthesized and tested for the ability to inhibit replication of HIV-1. Lithiation of acyclonucleosides with LDA followed by reaction with the electrophiles phenyl disulfide, diphenyl diselenide, 2,2'-dipyrdyl disulfide or 2,2'-dipyridyl diselenide afforded 6-(arylthio or arylseleno)acyclonucleosides 5a-c, 6, 7, 9, 15a-c, 17a-c. Compounds 19a-c and 20a-c were obtained by deprotection of corresponding TBDMS derivatives. Dehydrated products 16a, and 18a-c were also formed during the reactions. 5-Ethyl-6-(α-pyridylthio or α-pyridylseleno) disubstituted acyclouracils 6 and 7 were more active against HIV-1 in both MT-2 and CEM-IW cell lines than AZT, DDC, DDI or D4T. The EC50 of 6 against HIV-1 in CEM-IW cell was in the nanomolar range with a therapeutic index of 1100.

Antiviral Nucleosides. A Stereospecific, Total Synthesis of 2'-Fluoro-2'-deoxy-β-D-arabinofuranosyl Nucleosides

A general, total synthesis of (2'-fluoro-2'-deoxy-β-D-arabinofuranosyl)uracils 1a-d is described.A study of the coupling reaction beetwen 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide (7) and silylated pyrimidines 11a-d has resulted in a high overall yield for the five-step stereospecific synthesis of β-nucleosides.