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
• Article Data: 48

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

Description

N-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]pyrimidin-4-amine, also known as 2,4-Bis(trimethylsilyl)cytosine, is an organic compound that serves as an intermediate in the synthesis of pharmaceuticals. It is characterized by the presence of two trimethylsilyl groups attached to a pyrimidin-4-amine core, which contributes to its unique chemical properties and reactivity.

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

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

Downstream Products

• 85210-48-6 1-<2-(N-Benzoxycarbonyl-N-benzyl)aminoethoxymethyl>-4-amino-2-(1H)pyrimidinon 
• 78137-49-2 1-<<2-(benzoyloxy)ethoxy>methyl>cytosine 
• 109923-74-2 2',3',5'-tri-Obenzoyl-L-cytidine 
• 81252-62-2 (5-O-benzoyl-2,3-dideoxy-β-D-glycero-pentofuranosyl)cytosine 
• 117248-89-2 (5-O-benzoyl-2,3-dideoxy-α-D-glycero-pentofuranosyl)cytosine 
• 119555-43-0 1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine 
• 134790-40-2 C₂₃H₁₉F₂N₃O₆ 
• 134790-39-9 (2'-deoxy-2',2'-difluorocytidine)-3',5'-dibenzoate 
• 358348-70-6 cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane 
• 68724-12-9 1-<(2-hydroxyethoxy)methyl>cytosine 
• 134111-29-8 1-(2-deoxy-4-thio-3,5-di-O-toluoyl-α,β-D-erythro-pentofuranosyl)cytosine 
• 103824-50-6 2-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methyloxy>-1,3-propanediyl dibenzoate 
• 130914-74-8 2-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methoxy>-1,3-propanediyl bis-L-valinate 
• 20963-97-7 3',5'-di-O-benzoyl-2'-deoxycytidine 

Relevant articles and documents

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

In this paper we report the synthesis of N1-hexylthymine (1), N1-hexylcytosine (2), N1-hexylcytosine hydrobromide (3) and [(N1-hexylcytosinium)·(N1-hexylcytosine)] 2·[Cl2Hg(μ-Cl)

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

NMR studies of pyrimidinic nucleosides derived from 2,3-dideoxy-d-ribose with inhibitory activity on LINE-1 mobility

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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.

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.