1,4-Dioxane → 4-(5-Phenyl-2-pyridin-2-ylpyrimidin-4-yl)benzaldehyde

HRID 1674675Notes

Reaction equation

HRID 1674675 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:3]=1.[F-].[K+].[O:22]1[CH2:27][CH2:26]OCC1>O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:8]1([C:7]2[C:2]([C:8]3[CH:9]=[CH:10][C:26]([CH:27]=[O:22])=[CH:6][CH:7]=3)=[N:3][C:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[N:5][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 522689Potassium FluorideHCID 249037084-Chloro-5-phenyl-2-pyridin-2-ylpyrimidine

Product 1

HCID 591643624-(5-Phenyl-2-pyridin-2-ylpyrimidin-4-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalyst2×HCID 962WaterSolvent

Procedure

4-Chloro-5-phenyl-2-pyridin-2-ylpyrimidine (4-2; 0.15 g, 0.56 mmol), (4-formylphenyl)boronic (0.126 g, 0.840 mmol), bis(tri-t-butylphosphine)palladium(0) (0.014 g, 0.028 mmol) and anhydrous KF (0.107 g, 1.85 mmol) were stirred in 2 ml anhydrous dioxane under N2. The reaction was heated to reflux. After 15 min an additional sample of bis(tri-t-butylphosphine)palladium(0) (0.014 g, 0.028 mmol) was added and the reaction was heated at reflux overnight. The reaction was cooled and diluted with water. The mixture was extracted 3× with DCM. The combined organic phases was dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (dissolved sample in DCM, eluted with 98:2 DCM/EA) and provided an impure sample of 4-(5-phenyl-2-pyridin-2-ylpyrimidin-4-yl)benzaldehyde (4-3) that was used directly in the next transformation.

Workup

  1. temperatureThe reaction was heated to reflux
  2. temperaturethe reaction was heated
  3. temperatureat reflux overnight
  4. temperatureThe reaction was cooled
  5. extractionThe mixture was extracted 3× with DCM
  6. dry with materialThe combined organic phases was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography (dissolved sample in DCM, eluted with 98:2 DCM/EA)

Sources & evidence

ORD record
ord-af6f0c3be5a840faa84406023f318906
Source dataset
uspto-grants-2011_08
Patent number
US08003643B2

Reaction notes

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