ChemicalBook Produktkatalog Organische Chemie Organosiliciumverbindungen 4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine Struktur

4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Bezeichnung:4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

CAS-Nr941685-26-3

Englisch Name:4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

CBNumberCB42467652

SummenformelC12H18ClN3OSi

Molgewicht283.83

MOL-Datei941685-26-3.mol

4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine physikalisch-chemischer Eigenschaften

Siedepunkt	368.3±37.0 °C(Predicted)
Dichte	1.17±0.1 g/cm3(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
pka	3.00±0.30(Predicted)
Aussehen	White to off-white Solid
InChI	InChI=1S/C12H18ClN3OSi/c1-18(2,3)7-6-17-9-16-5-4-10-11(13)14-8-15-12(10)16/h4-5,8H,6-7,9H2,1-3H3
InChIKey	YWBDBLXIRAQZIH-UHFFFAOYSA-N
SMILES	C1=NC(Cl)=C2C=CN(COCC[Si](C)(C)C)C2=N1

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22
HazardClass	IRRITANT

Gefahreninformationscode (GHS)

4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden
4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine is used in the design and preparation of ruxolitinib-vorinostat conjugate derivatives which have dual inhibitory activity against Janus kinase (JAK) and histone deacetylase (HDAC).
Synthese

76513-69-4

3680-69-1

941685-26-3

Sodium hydride (340 mg, 60% dispersed in mineral oil) was added in two portions to a solution of 4-chloropyrrolo[2,3-d]pyrimidine (3a) (1.0 g, 6.5 mmol) in anhydrous DMF (15 mL) under the cooling conditions of an ice-salt bath, keeping the reaction temperature at 0 °C. The reaction temperature was controlled not to exceed 10 °C under nitrogen protection with continuous stirring for 1 hour. Subsequently, 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) (1.4 g, 8.5 mmol) was slowly added via syringe while ensuring that the temperature did not exceed 10 °C. The reaction mixture was gradually warmed to room temperature and stirring was continued overnight. After completion of the reaction, the reaction was quenched with water, extracted with ethyl acetate (EA) and the organic phase was dried over anhydrous sodium sulfate and concentrated. Purification by preparative fast chromatography (eluent: petroleum ether/ethyl acetate = 19:1) afforded 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (3b) (1.834 g, oily product) in 97% yield. Mass spectrum (ESI, m/z): 284 [M + H]+.
Einzelnachweise
[1] Patent: EP3360878, 2018, A1. Location in patent: Paragraph 0094; 0095
[2] Patent: CN107226814, 2017, A. Location in patent: Paragraph 0051-0052
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 20, p. 8336 - 8357
[4] Patent: EP3235819, 2017, A1. Location in patent: Paragraph 0122; 0123
[5] Patent: CN107513067, 2017, A. Location in patent: Paragraph 0082; 0083; 0084; 0085

4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine Upstream-Materialien And Downstream Produkte

4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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