2,4-Bis((trimethylsilyl)oxy)pyrimidine

Base Information

• Chemical Name: 2,4-Bis((trimethylsilyl)oxy)pyrimidine
• CAS No.: 10457-14-4
• Deprecated CAS: 1233524-07-6
• Molecular Formula: C10H20N2O2Si2
• Molecular Weight: 256.452
• European Community (EC) Number: 233-942-8
• NSC Number: 95115
• UNII: 36AFX6X4DF
• DSSTox Substance ID: DTXSID3065081
• Nikkaji Number: J129.456C
• Wikidata: Q81991966
• Mol file: 10457-14-4.mol

Synonyms:10457-14-4;2,4-Bis((trimethylsilyl)oxy)pyrimidine;Bis(O-trimethylsilyl)uracil;2,4-Bis(trimethylsilyloxy)pyrimidine;Bis(trimethylsilyl)uracil;2,4-BIS-TRIMETHYLSILANYLOXY-PYRIMIDINE;2,4-Bis(trimethylsiloxy)pyrimidine;2,4-Bis(trimethylsilyl)uracil;trimethyl-(2-trimethylsilyloxypyrimidin-4-yl)oxysilane;Pyrimidine, 2,4-bis(trimethylsiloxy)-;2,4-O-Bis(trimethylsilyl)uracil;Pyrimidine, 2,4-bis[(trimethylsilyl)oxy]-;Uracil, diTMS;36AFX6X4DF;Pyrimidine, 2,4-bis((trimethylsilyl)oxy)-;EINECS 233-942-8;NSC 95115;NSC-95115;2,4-BIS[(TRIMETHYLSILYL)OXY]PYRIMIDINE;o,o'-bis(trimethylsilyl)uracil;C10H20N2O2Si2;O,O-Bis-(trimethylsilyl)uracil;Uracil, bis-TMS;NSC95115;Uracil, 2TMS derivative;UNII-36AFX6X4DF;SCHEMBL1376899;DTXSID3065081;CHEBI:169506;Uracil, di(trimethylsilyl) deriv.;C10-H20-N2-O2-Si2;MFCD00054760;AKOS015892514;2,4-bis(trimethylsilyloxy)-1,3-diazine;DS-17739;Pyrimidine,2,4-bis[(trimethylsilyl)oxy]-;CS-0009692;FT-0658208;Pyrimidine, 2,4- bis[(trimethylsilyl)oxy]-;R10060

Chemical Property of 2,4-Bis((trimethylsilyl)oxy)pyrimidine

Chemical Property:

• Vapor Pressure: 0.0155mmHg at 25°C
• Melting Point: 31-33 °C
• Refractive Index: 1.461
• Boiling Point: 264.8 °C at 760 mmHg
• PKA: 1.11±0.20(Predicted)
• Flash Point: 114 °C
• PSA: 44.24000
• Density: 0.981 g/cm³
• LogP: 2.90400
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 256.10633095
• Heavy Atom Count: 16
• Complexity: 226

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,4-Bis((trimethylsilyl)oxy)pyrimidine ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OC1=NC(=NC=C1)O[Si](C)(C)C
• Uses: 2,4-Bis((trimethylsilyl)oxy)pyrimidine is an intermediate useful in the synthesis of Urea-13C,15N2 (U822502), which is a labeled urea. Physiological regulator of nitrogen excretion in mammals; synthesized in the liver as an end-product of protein catabolism and excreted in urine. Also occurs normally in skin. Emollient; diuretic.

Technology Process of 2,4-Bis((trimethylsilyl)oxy)pyrimidine

There total 24 articles about 2,4-Bis((trimethylsilyl)oxy)pyrimidine 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: 99.0%

chloro-trimethyl-silane (75-77-4) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → O,O'-bis-(trimethylsilyl)uracil (10457-14-4)

Guidance literature:

With 1,1,1,3,3,3-hexamethyl-disilazane; Heating;

DOI:10.1007/BF00777425

Reference yield: 99.0%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → O,O'-bis-(trimethylsilyl)uracil (10457-14-4)

Guidance literature:

With chloro-trimethyl-silane; for 24h; Reflux;

DOI:10.1007/s10593-020-02729-x

Reference yield: 96.0%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → O,O'-bis-(trimethylsilyl)uracil (10457-14-4)

Guidance literature:

DOI:10.1135/cccc19960389

upstream raw materials:

chloro-trimethyl-silane

2,4-dihydroxypyrimidine

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

uracil

Downstream raw materials:

trimethylsilyl acetate

tribenzoyl uridine

1-(methyl ester of 2,3,4-tri-O-benzoyl-β-D-galactopyranuronosyl)uracil

(1'RS)-1-<1'-(3''-Hydroxypropyloxy)-1'-phenylmethyl>uracil

Refernces

• 1、 Albert, Martin,De Souza, Dominic,Feiertag, Petra,Hoenig, Helmut. "A new concept for the preparation of beta-L- and beta-D-2',3'-dideoxynucleoside analogues.". . p. 3251 - 3254. Retrieved 2002.
• 2、 Tachallait, Hamza,Bouyahya, Abdelhakim,Talha, Aicha,Bakri, Youssef,Dakka, Nadia,Demange, Luc,Benhida, Rachid,Bougrin, Khalid. "Concise synthesis and antibacterial evaluation of novel 3-(1,4-disubstituted-1,2,3-triazolyl)uridine nucleosides". . . Retrieved 2018.
• 3、 Hyrosova,Fisera,Jame,Pronayova,Medvecky,Koos. "Diastereoselective synthesis of some carbocyclic 2′-oxa-3′-aza- nucleosides". . p. 10 - 17. Retrieved 2007.
• 4、 Ozerov, A. A.,Novikov, M. S.,Brel', A. K.,Andreeva, O. T.,Vladykov, G. V.,et al.. "SYNTHESIS AND ANTIVIRAL ACTIVITY OF NEW UNSATURATED PYRIMIDINE ACYCLONUCLEOSIDES". . p. 560 - 565. Retrieved 1991.
• 5、 Young, Robert J.,Shaw-Ponter, Sue,Hardy, George W.,Mills, Gail. "β-Anomer selectivity in 2′-deoxynucleoside synthesis: A novel approach using an acyl carbamate directing group". . p. 8687 - 8690. Retrieved 1994.
• 6、 Haraguchi, Kazuhiro,Kumamoto, Hiroki,Konno, Kiju,Yagi, Hideki,Tatano, Yutaka,Odanaka, Yuki,Shimbara Matsubayashi, Satoko,Snoeck, Robert,Andrei, Graciela. "Synthesis of 4′-substituted 2′-deoxy-4′-thiocytidines and its evaluation for antineoplastic and antiviral activities". . p. 4542 - 4555. Retrieved 2019.
• 7、 Gharpure, Santosh J.,Porwal, Suheel K.. "Stereoselective synthesis of oxa-bowls by nucleophilic addition to oxonium ions: Observation of nucleophile-dependent hydride migration". . p. 7277 - 7281. Retrieved 2013.
• 8、 Choi, Ka Wai,Brimble, Margaret A.. "Synthesis of spiroacetal-nucleosides as privileged natural product-like scaffolds". . p. 1424 - 1436. Retrieved 2009.
• 9、 Ait Ali, Mustapha,Belkharchach, Soumia,Ighachane, Hana,Lachgar, Abdessadek,Lazrek, Hassan B. "Efficient and selective catalytic N-Alkylation of pyrimidine by ammonium Sulfate?Hydro-thermal carbone under eco-friendly conditions". . . Retrieved 2020.
• 10、 Procopio, Antonio,Dalpozzo, Renato,De Nino, Antonio,Nardi, Monica,Oliverio, Manuela,Russo, Beatrice. "Er(OTf)3 as a valuable catalyst in a short synthesis of 2′,3′-dideoxy pyranosyl nucleosides via Ferrier rearrangement". . p. 2608 - 2612. Retrieved 2006.