Pyrimidine, 5-methyl-2,4-bis[(trimethylsilyl)oxy]-

Base Information

• Chemical Name: Pyrimidine, 5-methyl-2,4-bis[(trimethylsilyl)oxy]-
• CAS No.: 7288-28-0
• Deprecated CAS: 55170-67-7,1233524-08-7
• Molecular Formula: C11H22N2O2Si2
• Molecular Weight: 270.479
• NSC Number: 154616
• UNII: W28V4H6YE4
• DSSTox Substance ID: DTXSID1064615
• Nikkaji Number: J129.457A
• Wikidata: Q81991700
• Mol file: 7288-28-0.mol

Synonyms:7288-28-0;Bis(O-trimethylsilyl)thymine;Pyrimidine, 5-methyl-2,4-bis[(trimethylsilyl)oxy]-;5-Methyl-2,4-bis(trimethylsiloxy)pyrimidine;2,4-Bis(trimethylsilyl)thymine;Pyrimidine, 5-methyl-2,4-bis(trimethylsiloxy)-;5-Methyl-2,4-bis((trimethylsilyl)oxy)pyrimidine;trimethyl-(5-methyl-2-trimethylsilyloxypyrimidin-4-yl)oxysilane;O,O'-Bis(trimethylsilyl)thymine;Pyrimidine, 5-methyl-2,4-bis((trimethylsilyl)oxy)-;NSC 154616;NSC-154616;5-Methyl-2,4-bis[(trimethylsilyl)oxy]pyrimidine;Thymine, bis-TMS;NSC154616;o,o-bis(trimethylsilyl)thymine;C11H22N2O2Si2;SCHEMBL1335976;W28V4H6YE4;DTXSID1064615;C11-H22-N2-O2-Si2;MFCD00053571;AKOS024319173;O,O'-Bis(trimethylsilyl)thymine, 97%;5-methyl-2,4-bis(trimethylsilyloxy)pyrimidine;Pyrimidine, 2,4-dihydroxy-5-methyl, bis-TMS;5-methyl-2,4-bis[( trimethylsilyl)oxy ]pyrimidine

Chemical Property of Pyrimidine, 5-methyl-2,4-bis[(trimethylsilyl)oxy]-

Chemical Property:

• Appearance/Colour: colourless solid, very sensitive to moisture
• Vapor Pressure: 0.00356mmHg at 25°C
• Melting Point: 73-75 °C(lit.)
• Refractive Index: 1.463
• Boiling Point: 290.6 °C at 760 mmHg
• PKA: 1.50±0.29(Predicted)
• Flash Point: 129.6 °C
• PSA: 44.24000
• Density: 0.974 g/cm³
• LogP: 3.21240
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 270.12198102
• Heavy Atom Count: 17
• Complexity: 251

Purity/Quality:

98% ^*data from raw suppliers

O,O′-Bis(trimethylsilyl)thymine 97% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: CC1=CN=C(N=C1O[Si](C)(C)C)O[Si](C)(C)C
• Uses: O,O′-Bis(trimethylsilyl)thymine is a reactive intermediate for the preparation of nucleosides.

Technology Process of Pyrimidine, 5-methyl-2,4-bis[(trimethylsilyl)oxy]-

There total 19 articles about Pyrimidine, 5-methyl-2,4-bis[(trimethylsilyl)oxy]- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

thymin (65-71-4,28806-14-6,691841-57-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0)

Guidance literature:

With ammonium bisulphate; In 1,2-dichloro-ethane; Reflux; Inert atmosphere; Schlenk technique;

DOI:10.3390/molecules22010084

Reference yield: 100.0%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + thymin (65-71-4,28806-14-6,691841-57-3) → 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0)

Guidance literature:

In acetonitrile; at 25 ℃; for 4h;

DOI:10.3390/ijms23020915

Reference yield: 99.0%

chloro-trimethyl-silane (75-77-4) + thymin (65-71-4,28806-14-6,691841-57-3) → 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0)

Guidance literature:

With 1,1,1,3,3,3-hexamethyl-disilazane; Ambient temperature;

DOI:10.1007/BF00777425

upstream raw materials:

Hexamethyldisiloxane

2,4-dihydroxy-5-methylpyrimidine

1,1,1,3,3,3-hexamethyl-disilazane

N,N-bis(trimethylsilyl)acetamide

Downstream raw materials:

trans-1-(3-Oxoprop-1-enyl)thymine

(S)-1-{[2-O-4,4'-dimethoxytrityl-1-(hydroxymethyl)ethoxy]methyl}thymine

1-{(R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-hydroxy-propoxymethyl}-5-methyl-1H-pyrimidine-2,4-dione

1-(3,5-di-O-benzyl-2-deoxy-α,β-D-erythro-pentofuranosyl)thymine

Refernces

• 1、 Nakaya, Manabu,Ohtani, Ryo,Sugimoto, Kunihisa,Nakamura, Masaaki,Lindoy, Leonard F.,Hayami, Shinya. "Molecular Assemblies of Metal Complexes via Base-Pairing of Nucleic Acids in the Crystalline State". . p. 7232 - 7237. Retrieved 2017.
• 2、 . "-". . p. 324 - 328. Retrieved 1985.
• 3、 Voss, Jürgen,Otzen, Dirk,Adiwidjaja, Gunadi. "Thiosugars, 17. Preparation and structure of a novel deoxythionucleoside". . p. 553 - 556. Retrieved 2018.
• 4、 Church, Kevin M.,Holloway, Liesel M.,Matley, Ryan C.,Brower III, Robert J.. "Efficient pyrimidine N-1-alkylation via activation of electron rich olefins with oxoammonium salts: Synthesis of Methoxy TEMPO substituted pyrimidine nucleoside analogs". . p. 1723 - 1738. Retrieved 2004.
• 5、 Lin,Luo,Liu. "Synthesis of 1-[cis-2-hydroxy-cis-3-(hydroxymethyl)-cyclobutyl]thymine, a novel method for the synthesis of cyclobutyl nucleosides and related compounds". . p. 245 - 254. Retrieved 1994.
• 6、 Frei, Sibylle,Katolik, Adam K.,Leumann, Christian J.. "Synthesis, biophysical properties, and RNase H activity of 6’-difluoro[4.3.0]bicyclo-DNA". . p. 79 - 88. Retrieved 2019.
• 7、 Kumamoto, Hiroki,Nakai, Takahito,Haraguchi, Kazuhiro,Nakamura, Kazuo T.,Tanaka, Hiromichi,Baba, Masanori,Cheng, Yung-Chi. "Synthesis and anti-human immunodeficiency virus activity of 4′-branched (±)-4′-thiostavudines". . p. 7861 - 7867. Retrieved 2006.
• 8、 Andreeva, Olga V.,Garifullin, Bulat F.,Zarubaev, Vladimir V.,Slita, Alexander V.,Yesaulkova, Iana L.,Saifina, Liliya F.,Shulaeva, Marina M.,Belenok, Maya G.,Semenov, Vyacheslav E.,Kataev, Vladimir E.. "Synthesis of 1,2,3-triazolyl nucleoside analogues and their antiviral activity". . p. 473 - 490. Retrieved 2020/09/22.
• 9、 Behrouz, Somayeh,Soltani Rad, Mohammad Navid,Piltan, Mohammad Amin. "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". . p. 113 - 124. Retrieved 2019/07/30.