Water → 4-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1042289

Reaktionsgleichung

Reaktionsgleichung von HRID 1042289
C([O-])(=O)C.[K+].Cl[C:7]1[N:12]=[CH:11][N:10]=[C:9]2[NH:13][N:14]=[CH:15][C:8]=12.[F:16][C:17]1[C:22](B(O)O)=[CH:21][CH:20]=[CH:19][N:18]=1.O>CCO>[F:16][C:17]1[C:22]([C:7]2[N:12]=[CH:11][N:10]=[C:9]3[NH:13][N:14]=[CH:15][C:8]=23)=[CH:21][CH:20]=[CH:19][N:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidineHCID 517044Potassium AcetateHCID 27832702-Fluoropyridine-3-boronic acid

Produkt 1

HCID 596273834-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of potassium acetate (13 g, 130 mmol), PdCl2(P-t-Bu2Ph)2 (1.1 g, 1.7 mmol), 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (6.70 g, 43 mmol) and 2-fluoropyridin-3-ylboronic acid (7.3 g, 52 mmol) in EtOH (300 ml)-water (100 ml) was sonicated until the solid became a fine powder and degassed under vacuum. The mixture was refluxed under N2 overnight. After cooling to rt solvent was removed in vacuo and to the residues was added water (200 ml) and NaHCO3 (sat. 150 ml). The mixture was stirred for 15 min. The solid was filtered and washed with water. The solid was dissolved in MeOH-DCM and preloaded on silica gel and purified by flash chromatography eluting with MeOH/DCM (1-5%) to give 4-(2-fluoropyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidine. MS Found: (ESI pos. ion) m/z 216 (M+H+).

Aufarbeitung

  1. customwas sonicated until the solid
  2. customdegassed under vacuum
  3. temperatureThe mixture was refluxed under N2 overnight
  4. customwas removed in vacuo and to the residues
  5. additionwas added water (200 ml) and NaHCO3 (sat. 150 ml)
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. dissolutionThe solid was dissolved in MeOH-DCM
  9. custompurified by flash chromatography
  10. washeluting with MeOH/DCM (1-5%)

Quellen und Nachweise

ORD-Eintrag
ord-5df778c95f4949e295779504861f6e80
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557830B2

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