18037-10-0

Basic information

• Product Name: N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine
• Synonyms: BIS(TRIMETHYLSILYL)CYTOSINE;4-Pyrimidinamine, N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-;n-(trimethylsilyl)-2-[(trimethylsilyl)oxy]-4-pyrimidinamin;N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]-4-pyrimidinamine;O2,N4-Bis(trimethylsilyl)cytosine;Pyrimidine, 2-(trimethylsiloxy)-4-[(trimethylsilyl)amino]-;N-(trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine;Bis-(Trimethylsilyl) Cytosine (BSC)
• CAS NO: 18037-10-0
• Molecular Formula: C₁₀H₂₁N₃OSi₂
• Molecular Weight: 255.46
• EINECS: 241-945-0
• Mol File: 18037-10-0.mol

Chemical Properties

• Melting Point: 122°C
• Boiling Point: 123 °C
• Flash Point: 65°C
• Appearance: withe powder
• Density: 0.994 g/cm³
• Vapor Pressure: 0.00112mmHg at 25°C
• Refractive Index: 1.493
• PKA: 4.96±0.10(Predicted)
• CAS DataBase Reference: N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine(18037-10-0)
• EPA Substance Registry System: N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine(18037-10-0)

Safety Data

• TSCA: Yes
• Hazardous Substances Data: 18037-10-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine is used as an intermediate in the synthesis of 1'-Epi Gemcitabine Hydrochloride (E588510), which is an α-Anomer of Gemcitabine. N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine plays a crucial role in the development of novel therapeutic agents with potential applications in the treatment of various diseases and conditions.

InChI:InChI=1/C10H21N3OSi2/c1-15(2,3)13-9-7-8-11-10(12-9)14-16(4,5)6/h7-8H,1-6H3,(H,11,12,13)

Upstream product

• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 71-30-7 Cytosine 
• 38860-08-1 2-(trimethylsiloxy)-1-(trimethylsilyl)propene 
• 75-77-4 chloro-trimethyl-silane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 72525-60-1 hexamethyldisilazan 
• 71-30-7 cytosine 
• 71-30-7 6-amino-2-hydroxypyrimidine 
• 17857-70-4 tri-n-butyl-cyclopropyltin 
• 50271-92-6 5-Bromo-2,4-O,N-bis-trimethylsilylcytosine 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 10416-59-8 N,O-Bis(trimethylsilyl)acetamide 

Downstream Products

• 1213750-73-2 2'-deoxy-2',2'-difluoro-3',5'-di-O-benzoyl-cytidine hydrochloride 
• 896109-84-5 1-(2'-deoxy-2',2'-difluoro-5-benzoyl-3-(4-phenyl)benzoyl-β-D-arabinofuranosyl)-4-aminopyrimidine-2-one 
• 2857-97-8 trimethylsilyl bromide 
• 1155863-81-2 C₂₃H₁₉F₂N₃O₆ 
• 147027-10-9 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate 
• 20963-97-7 C₂₃H₂₁N₃O₆ 
• 20963-97-7 3',5'-di-O-benzoyl-2'-deoxycytidine 
• 130914-74-8 2-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methoxy>-1,3-propanediyl bis-L-valinate 
• 103824-50-6 2-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methyloxy>-1,3-propanediyl dibenzoate 
• 134111-29-8 1-(2-deoxy-4-thio-3,5-di-O-toluoyl-α,β-D-erythro-pentofuranosyl)cytosine 
• 358348-70-6 cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane 
• 134790-40-2 C₂₃H₁₉F₂N₃O₆ 
• 134790-39-9 (2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate 
• 119555-43-0 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine 

Relevant articles and documents

Experimental and theoretical study of thymine and cytosine derivatives: The crucial role of weak noncovalent interactions

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A stereoselective method for the direct preparation of 2'-deoxycytidine

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Molecular design, chemical synthesis, and evaluation of cytosine-carbohydrate hybrids for selective recognition of a single guanine bulged duplex DNA

The designed cytosine-carbohydrate hybrid molecule selectively recognized and stabilized the bulged duplex DNA possessing the complementary bulged DNA base, guanine, while the nucleotide base itself did not exhibit any such ability. It was also found that

A new route to 2'-C-methylene nucleoside analogs, inhibitors of ribonucleotide reductase

Glycosyl phenyl sulfone obtained in 4 steps from isosaccharino-lactone was converted into a 2'-C-acetoxymethylfuranoid glycal with SmI2-HMPA. Coupling of this glycal with silylated thymine or cytidine in the presence of Pd(0) led, after deprote

Convergent Total Synthesis of Hikizimycin Enabled by Intermolecular Radical Addition to Aldehyde

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Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine

Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.

A preparation method of lamivudine

The invention discloses a method for preparation of lamivudine. Refined pure 5 S - (cytosine base - 1 ') - 1, 3 - oxathiolane - 2 - ethoxy carbonyl - (1' R, 2'S, 3' R) - menthyl ester; in the weak base and the solvent removed under the condition of chiral L - menthol to get a product of lamivudine. The material of the invention is cheap, the reagents used in the environmental protection, steps is relatively short, mild reaction conditions, atom utilization rate high, high yield, high chemical purity of the obtained product, reach the medical standard, suitable for large-scale production of lamivudine preparation method.

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.

Synthetic method for lamivudine

The invention provides a synthetic method for lamivudine. The synthetic method comprises the following steps: cheap easily-available dihaloacetic acid is used as a raw material, the dihaloacetic acidand L-menthol are subjected to condensation, hydrolysis is performed to obtain menthyl glyoxylate, the menthyl glyoxylate and 2,5-dihydroxy-1,4-dithiane are subjected to condensation, halogenation isperformed, the halogenated product and silanized cytosine are subjected to coupling, reduction is performed, the reduced product and salicylic acid are subjected to salt formation to obtain the a salicylate, and finally recrystallization is performed to obtain the optically-pure lamivudine. According to the method provided by the invention, the raw materials used in the whole synthetic process arecheap and easy to obtain, the synthetic process is simple, the synthetic conditions are mild, so that the synthetic costs of the lamivudine are greatly reduced; the raw material utilization rate andreaction selectivity are high, so that the yield of the obtained lamivudine is higher; and at the same time, a chiral substrate is easily removed during the synthesis, three waste (waste water, wastegas and solid waste) generated in the method are less, and the method is suitable for industrialized large-scale production of the lamivudine.

Asymmetric synthesis method of lamivudine

The invention provides an asymmetric synthesis method of lamivudine. The synthesis method comprises: carrying out condensation on L-menthyl chloroformate used as a starting raw material and geminal dihaloethanol, hydrolyzing to obtain an acetaldehyde alcohol optically-active ester, carrying out condensation with 5,5-dihydroxy-1,4-dithiane to obtain trans 5-hydroxy-1,3-oxathiolane-2-methyl optically-active ester, acetylating, coupling with silanized cytosine, and finally removing the chiral auxiliary agent to obtain the product lamivudine. According to the present invention, the raw materials used in the entire synthesis process are cheap and readily available, and have high utilization rate, such that the synthesis cost of lamivudine is substantially reduced; the synthesis process is simple, the synthesis conditions are mild, the yield of the obtained lamivudine is high, the chiral substrate is easily removed during the synthesis, and the generated three-waste pollutants are less; andthe method is suitable for industrial large-scale production of lamivudine.