4-Pyrimidinamine, N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-

Base Information

• Chemical Name: 4-Pyrimidinamine, N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-
• CAS No.: 18037-10-0
• Molecular Formula: C10H21N3OSi2
• Molecular Weight: 255.467
• Hs Code.: 2933599090
• European Community (EC) Number: 241-945-0
• UNII: 52FEX9LR9R
• DSSTox Substance ID: DTXSID30884794
• Nikkaji Number: J133.583I
• Wikidata: Q72514585
• Mol file: 18037-10-0.mol

Synonyms:18037-10-0;Bis(trimethylsilyl)cytosine;n-(trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine;4-Pyrimidinamine, N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-;N-trimethylsilyl-2-trimethylsilyloxypyrimidin-4-amine;O2,N4-Bis(trimethylsilyl)cytosine;52FEX9LR9R;O,N-Bis(trimethylsilyl)cytosine;4-Pyrimidinamine, N-(trimethylsilyl)-2-((trimethylsilyl)oxy)-;EINECS 241-945-0;N-(Trimethylsilyl)-2-((trimethylsilyl)oxy)pyrimidin-4-amine;Pyrimidine, 2-(trimethylsiloxy)-4-[(trimethylsilyl)amino]-;N-(Trimethylsilyl)-2-((trimethylsilyl)oxy)-4-pyrimidinamine;N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]-4-pyrimidinamine;Cytosine, bis-TMS;UNII-52FEX9LR9R;C10H21N3OSi2;SCHEMBL396081;2,4-Bis(trimethylsilyl)cytosine;DTXSID30884794;C10-H21-N3-O-Si2;BIS(TRIMETHYLSILYL)CYTOSINE?;MFCD00047357;AKOS015901737;Pyrimidine, 2-hydroxy-4-amino, di-TMS;CS-0133103;FT-0743454;Cytosine, N-trimethylsilyl-, trimethylsilyl ether;2-(Trimethylsiloxy)-4-(trimethylsilylamino)pyrimidine;N-(trimethylsilyl)-2-(trimethylsilyloxy)pyrimidin-4-amine

Chemical Property of 4-Pyrimidinamine, N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-

Chemical Property:

• Appearance/Colour: withe powder
• Vapor Pressure: 0.00112mmHg at 25°C
• Melting Point: 122 °C
• Refractive Index: 1.493
• Boiling Point: 300.4 °C at 760 mmHg
• PKA: 4.96±0.10(Predicted)
• Flash Point: 135.5 °C
• PSA: 47.04000
• Density: 0.994 g/cm³
• LogP: 3.01010
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 255.12231537
• Heavy Atom Count: 16
• Complexity: 225

Purity/Quality:

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

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)NC1=NC(=NC=C1)O[Si](C)(C)C
• Uses: 2,4-Bis(trimethylsilyl)cytosine is an intermediate used in the synthesis of 1’-Epi Gemcitabine Hydrochloride (E588510), which is an α-Anomer of Gemcitabine.

Technology Process of 4-Pyrimidinamine, N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-

There total 13 articles about 4-Pyrimidinamine, N-(trimethylsilyl)-2-[(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: 93.0%

Cytosine (71-30-7) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → 2,4-O,N-bis(trimethylsilyl)cytosine (18037-10-0)

Guidance literature:

With chloro-trimethyl-silane; for 6h; Heating;

DOI:10.1016/j.bmcl.2005.06.073

Reference yield:

chloro-trimethyl-silane (75-77-4) + Cytosine (71-30-7) → 2,4-O,N-bis(trimethylsilyl)cytosine (18037-10-0)

Guidance literature:

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

DOI:10.1021/jo00086a032

Reference yield:

N,O-Bis(trimethylsilyl)acetamide (10416-59-8,132255-83-5) + Cytosine (71-30-7) → 2,4-O,N-bis(trimethylsilyl)cytosine (18037-10-0)

Guidance literature:

In acetonitrile;

DOI:10.1016/S0040-4020(01)80740-7

upstream raw materials:

chloro-trimethyl-silane

Cytosine

N,O-Bis(trimethylsilyl)acetamide

N,O-Bis(trimethylsilyl)trifluoroacetamide

Downstream raw materials:

1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one

trimethylsilyl bromide

C₂₃H₁₉F₂N₃O₆

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate

Refernces

• 1、 Kjell, Douglas P.. "A stereoselective method for the direct preparation of 2'-deoxycytidine". . p. 301 - 303. Retrieved 1997.
• 2、 Pontikis,Wolf,Monneret,Florent. "A new route to 2'-C-methylene nucleoside analogs, inhibitors of ribonucleotide reductase". . p. 3523 - 3526. Retrieved 1995.
• 3、 Fujino, Haruka,Fukuda, Takumi,Nagatomo, Masanori,Inoue, Masayuki. "Convergent Total Synthesis of Hikizimycin Enabled by Intermolecular Radical Addition to Aldehyde". supporting information. p. 13227 - 13234. Retrieved 2020/09/01.
• 4、 -. "A preparation method of lamivudine". Paragraph 0042; 0061-0063. . Retrieved 2019/04/02.