Sodium hydride → 2-bromo-6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine

HRID 905987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 905987
[Br:1][C:2]1[N:3]=[C:4]2[CH:10]=[C:9]([CH3:11])[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[CH:10]=[C:9]([CH3:11])[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

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 714334512-bromo-6-methyl-5H-pyrrolo[2,3-b]pyrazine

Produkt 1

HCID 866423052-bromo-6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazineAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Bromo-6-methyl-5H-pyrrolo[2,3-b]pyrazine (0.300 g, 1.41 mmol) was dissolved in DMF (5 mL) and cooled down to 0° C. NaH (60%, 68 mg, 1.70 mmol) was added slowly. After the addition was complete stirring was continued for 30 minutes at 0° C. (2-Chloromethoxy-ethyl)-trimethyl-silane (0.30 mL, 1.70 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 (40 g SiO2, hexanes/EtOAc 0-35% EtOAc) to give 340 mg of 2-bromo-6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine as a yellow liquid (70% yield).

Aufarbeitung

  1. additionAfter the addition
  2. temperatureto warm up overnight
  3. customThe reaction was quenched with H2O
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by SiO2 chromatography (40 g SiO2, hexanes/EtOAc 0-35% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-f46a3e69f1c04dd38da9b46d9a12bffa
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012974B2

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