17331-61-2

Basic information

• Product Name: 2 4-BIS(TRIMETHYLSILYL)-6-AZAURACIL
• Synonyms: 2 4-BIS(TRIMETHYLSILYL)-6-AZAURACIL;2,4-Triazine,3,5-bis[(trimethylsilyl)oxy]-1;4-triazine,3,5-bis[(trimethylsilyl)oxy]-2;bis(Trimethylsilyl)-6-azauracil;3,5-bis(trimethylsilyloxy)-1,2,4-triazine;1,2,4-Triazine,3,5-bis[(trimethylsilyl)oxy]-;2 4-BIS(TRIMETHYLSILYL)-6-AZAURACIL 97%;3,5-Bis(trimethylsiloxy)-1,2,4-triazine
• CAS NO: 17331-61-2
• Molecular Formula: C₉H₁₉N₃O₂Si₂
• Molecular Weight: 257.44
• EINECS: 241-353-2
• Mol File: 17331-61-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 269.1°Cat760mmHg
• Flash Point: 116.5°C
• Appearance: /
• Density: 1.011g/cm³
• Vapor Pressure: 0.0123mmHg at 25°C
• Refractive Index: 1.46
• CAS DataBase Reference: 2 4-BIS(TRIMETHYLSILYL)-6-AZAURACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 2 4-BIS(TRIMETHYLSILYL)-6-AZAURACIL(17331-61-2)
• EPA Substance Registry System: 2 4-BIS(TRIMETHYLSILYL)-6-AZAURACIL(17331-61-2)

Safety Data

• Hazardous Substances Data: 17331-61-2(Hazardous Substances Data)

Usage

General Description

2,4-BIS(TRIMETHYLSILYL)-6-AZAURACIL is a chemical compound that is a derivative of uracil. It is made up of two trimethylsilyl groups attached to the 2 and 4 positions of the uracil ring, and an additional nitrogen atom at the 6 position. 2 4-BIS(TRIMETHYLSILYL)-6-AZAURACIL is commonly used as a building block in organic synthesis and as a precursor for the preparation of various functionalized uracil derivatives. It is also used as a reagent in the synthesis of nucleoside analogs and other pharmaceutical compounds. Additionally, 2,4-BIS(TRIMETHYLSILYL)-6-AZAURACIL is being studied for its potential applications in medicinal chemistry and drug discovery.

InChI:InChI=1/C9H19N3O2Si2/c1-15(2,3)13-8-7-10-12-9(11-8)14-16(4,5)6/h7H,1-6H3

Upstream product

• 461-89-2 6-azauracil 
• 75-77-4 chloro-trimethyl-silane 
• 4039-32-1 lithium hexamethyldisilazane 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 461-89-2 3,5-dihydroxy-1,2,4-triazine 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 267667-52-7 (2R,5S)- and (2R,5R)-1-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-3,5(2H,4H)-dione 
• 1013470-68-2 2-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-1,2,4-triazin-3,5(2H,4H)-dione 
• 61959-06-6 2-(2-oxo-2-phenylethyl)-1,2,4-triazine-3,5(2H,4H)-dione 
• 61959-08-8 2-(2-oxo-2-(4-fluorophenyl)ethyl)-1,2,4-triazine-3,5(2H,4H)-dione 
• 29725-46-0 2-(tri-O-benzyl-β-D-ribofuranosyl)-2H-[1,2,4]triazine-3,5-dione 
• 2169-64-4 2',3',5'-tri-O-acetyl-6-azauridine 
• 1146632-14-5 C₂₉H₂₃N₃O₉ 
• 1234873-91-6 C₂₉H₂₃N₃O₉ 
• 105015-84-7 2-(tri-O-benzoyl-β-D-xylofuranosyl)-2H-[1,2,4]triazine-3,5-dione 
• 1146632-13-4 C₂₉H₂₃N₃O₉ 
• 206269-47-8 1-(2',3',5'-tri-O-benzoyl-β-L-ribofuranosyl)-6-azauracil 
• 31952-61-1 5-phenyl-1,2,4-triazin-3(2H)-one 
• 61959-17-9 2-(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-2H-[1,2,4]triazine-3,5-dione 

Relevant articles and documents

Synthesis and reactions of some glycosylamine derivatives of 6-azauracil nucleosides

Reaction of the silylated 6-azauracil (2) with 2-acetamido-1,3,4,6-tetra- O-acetyl-2-deoxy-D-glucose (3) gave 1-(2-acetamido-3,4,6-tri-O-acetyl-2- deoxy-β-D-glucopyranosyl)-6-azauracil (4), which gave the free nucleoside 5 on deblocking. Acetalation of 5 gave the monoacetal 6 which was oxidized into the ketone 7. Reduction of 7 gave the allo-nucleoside 9 which on hydrolysis afforded the free nucleoside 10. Alternatively, compound 10 was obtained from mesylation of 6 to give 8 followed by subsequent acetolysis and hydrolysis.

Chitosan–silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method

Abstract: The presilylation of purine and pyrimidine nucleobases as well as other related N-heterocycles with HMDS utilizing chitosan–silica sulfate nanohybrid (CSSNH) is described. CSSNH is proved to be a useful, highly efficient and eco-friendly heterogeneous nanohybrid catalyst for silylation of nucleobases. The presilylated nucleobases then underwent the reaction with different sources of carbon electrophiles to afford the desired N-alkyl-substituted derivatives in good-to-excellent yields. CSSNH exhibits several advantageous involving ease of handling and preparation, low cost, reusability and environmental benignity. These unique properties render the CSSNH to be an ideal candidate for use in green industrial processes. Graphic abstract: [Figure not available: see fulltext.].

HMDS/KI a simple, a cheap and efficient catalyst for the one-pot synthesis of N-functionalized pyrimidines

The syntheses of N-Alkylpyrimidine derivatives by reacting pyrimidin-2,4-diones with appropriate alkyl halide under microwave irradiation at 400 W were compared to the conventional synthesis route. These methodologies are regioselective and compatible with numerous substrates and furnish the corresponding N-alkylpyrimidines in good yields using a cheap catalyst HMDS/KI in MeCN. A comparison study between these two different modes of heating was investigated.

Synthesis of new oxabicyclo[3.3.0]octane nucleoside analogues with pyrimidine bases

Synthesis of new nucleosides with an oxabiciclo[3.3.0]octane fragment in the sugar moiety was performed by Vorbruggen nucleoside synthesis with silylated pyrimidine bases: 5-FU, 5-ClU, 5-BrU, C and 6-aza-U. The compounds were characterized by IR, MS, 1H-NMR and 13C-NMR spectra and tested for their antitumor activity comparatively with U-34 and 5IU-34. Our study points out that Cl-U-34, Br-U-34 and I-U-34 might be more efficient than U-34 against the multiplication of cancer cells, like Jurkat T lymphoblasts.