Sodium hydride → 2-Bromo-7-methyl-5-[[2-(trimethylsilyl)ethoxy]methyl]-5H-pyrrolo[2,3-b]pyrazine

HRID 905994Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]2[C:10]([CH3:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([CH3:11])=[CH:9][N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Bromo-7-methyl-5H-pyrrolo[2,3-b]pyrazine (0.279 g, 1.321) was dissolved in DMF (5 mL) and cooled down to 0° C. NaH (60%, 63 mg, 1.58 mmol) was added slowly. After the addition was complete stirring was continued for 30 minutes at 0° C. (2-Chloromethoxy-ethyl)-trimethyl-silane (0.28 mL, 1.58 mmol) was added and the reaction mixture was allowed to warm up overnight. The reaction was quenched with H2O. The aqueous layer was extracted with EtOAc. The organic layer was dried (MgSO4), filtered, concentrated, and purified by SiO2 chromatography (24 g SiO2, hexanes/EtOAc 0-35% EtOAc) to give 340 mg of 2-bromo-7-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine as a yellow liquid (77% yield).

Workup

additionAfter the addition
temperatureto warm up overnight
customThe reaction was quenched with H2O
extractionThe aqueous layer was extracted with EtOAc
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
custompurified by SiO2 chromatography (24 g SiO2, hexanes/EtOAc 0-35% EtOAc)

Sources & evidence

ORD record: ord-de6937adf45b4d69bd3915e8f660c527
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012974B2

Reaction notes

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