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

HRID 905925Notes

Reaction equation

HRID 905925 reaction equation
[H-].[Na+].[Br:3][C:4]1[N:5]=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1.[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>CCCCCC.CN(C)C=O>[Br:3][C:4]1[N:5]=[C:6]2[CH:12]=[CH:11][N:10]([CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 575165972-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazineYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Conditions

Temperature
2.5 °C

Procedure

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.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-94fcd548ca3d42a1ae62c59bd39555d7
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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