Potassium Hydroxide → 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

HRID 246631

Reaktionsgleichung

Reaktionsgleichung von HRID 246631
[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([O:13]C)=[O:12])=[CH:9][N:8](COC(=O)C(C)(C)C)[C:5]2=[N:6][CH:7]=1.[OH-].[K+]>O.O1CCOCC1>[Br:1][C:2]1[N:3]=[C:4]2[C:10]([C:11]([OH:13])=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 86677991methyl 2-bromo-5-(pivaloyloxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate

Produkt 1

HCID 866778972-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-bromo-5-(pivaloyloxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylate (370 mg, 1 mmol), potassium hydroxide (280 mg, 5 mmol) in 2.5 mL of water and 5 mL of 1,4-dioxane was heated to reflux for 90 mins. The reaction mixture was cooled to room temperature, solvent evaporated, residue acidified with 1N HCl, filtered and dried to give 2-bromo-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid as a brown solid (320 mg, crude), material used in the next step without further purification. LCMS: (M+H)+=242/244; (M+Na)+=264/266.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 90 mins
  3. customsolvent evaporated
  4. filtrationfiltered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a0c4d275b6f5440890b479b0e86dc7d9
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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