Sodium Carbonate → 4-(Pyrimidin-2-yl)benzaldehyde

HRID 131631Notes

Reaction equation

HRID 131631 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:14]1[CH:15]=[CH:16][CH:17]=[N:18][C:13]=1[C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 783452-BromopyrimidineHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 127037224-(Pyrimidin-2-yl)benzaldehydeYield 73.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a degassed suspension of 4-formylphenylboronic acid (100 mg), 2-bromopyrimidine (107 mg) and sodium carbonate (212 mg) in acetonitrile (2 ml)/water (2 ml) was added freshly prepared tetrakis(triphenylphosphine)palladium(0), (40 mg) and the mixture was refluxed under nitrogen, for 20 hrs. The cooled reaction mixture was diluted with water and extracted with ethyl acetate (×2). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with iso-hexane/ethyl acetate (75:25) to afford the sub-title compound as a solid (90 mg).

Workup

  1. temperaturethe mixture was refluxed under nitrogen, for 20 hrs
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate (×2)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography over silica
  8. washeluting with iso-hexane/ethyl acetate (75:25)

Sources & evidence

ORD record
ord-d3f21f00e2414531b4f4c993a8b1d7f5
Source dataset
uspto-grants-2008_06
Patent number
US07384951B2

Reaction notes

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