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

HRID 1042289

Reaction equation

HRID 1042289 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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+).

Workup

  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%)

Sources & evidence

ORD record
ord-5df778c95f4949e295779504861f6e80
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Linked notes

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