Sodium hydride → 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine

Participants

Role	Name	HCID	Charge
Reactant	Sodium hydride	HCID 24758	—
Reactant	2-Chloromethyl 2-(trimethylsilyl)ethyl ether	HCID 2724271	—
Reactant	2-bromo-5H-pyrrolo[2,3-b]pyrazine	HCID 25067308	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Hexane	HCID 8058	—
Product	2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine	HCID 57516597	66%

Reaction Conditions

Temperature	2.5 °C

Reaction Steps

Sodium hydride (60% in mineral oil, 0.800 g, 20 mmol) was washed with hexane then taken up in 30 mL of N,N-dimethylformamide and cooled to 0-5° C. 2-Bromo-5H-pyrrolo[2,3-b]pyrazine (3.0 g, 15 mmol) was added, then SEMCl (3.5 mL, 20 mmol). The mixture was stirred at room temperature for 3 h, then concentrated. Column chromatography afforded 3.25 g (65%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08012974B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-94fcd548ca3d42a1ae62c59bd39555d7
Source note	uspto-grants-2011_09