Potassium Carbonate → 5-(5-fluoro-pyridin-2-yl)-2-hydroxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one

HRID 2046216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2046216
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]3[N:20]=[C:21]([CH2:23][O:24]C(=O)C)[CH:22]=[C:16]3[C:15]2=[O:28])=[N:12][CH:13]=1>CO>[F:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]3[N:20]=[C:21]([CH2:23][OH:24])[CH:22]=[C:16]3[C:15]2=[O:28])=[N:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 67975679Acetic acid 5-(5-fluoro-pyridin-2-yl)-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester

Produkt 1

HCID 679741735-(5-fluoro-pyridin-2-yl)-2-hydroxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-oneAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Potassium carbonate (63 mg, 0.46 mmol) was added to a stirred suspension of acetic acid 5-(5-fluoro-pyridin-2-yl)-4-oxo-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazin-2-ylmethyl ester (70 mg, 0.23 mmol) in MeOH (1 mL). The mixture was stirred at room temperature for 16 hours. The solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica, 7 N solution of ammonia in MeOH in DCM 0/100 to 10/90). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-(5-fluoro-pyridin-2-yl)-2-hydroxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (30 mg, 50% yield) as a white solid.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica, 7 N solution of ammonia in MeOH in DCM 0/100 to 10/90)
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f9bb8c2f1ba14d67b4351b1d0803d262
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592422B2

Notizen zur Reaktion

Wird geladen…