Sodium Carbonate → 2-(pyrimidin-5-yl)benzaldehyde

HRID 1988053Notes

Reaction equation

HRID 1988053 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O)=[O:2].Br[C:13]1[CH:14]=[N:15][CH:16]=[N:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[N:15]1[CH:14]=[C:13]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[O:2])[CH:18]=[N:17][CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 783445-BromopyrimidineHCID 2921892-Formylphenylboronic acid

Product 1

HCID 38078602-(pyrimidin-5-yl)benzaldehydeYield 59.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vial (20 ml) was charged with 2-formylphenylboronic acid (290 mg, 2.0 mmol), 5-bromo-pyrimidine (316 mg, 2.0 mmol) and 8 ml of acetonitrile. To this mixture was added 4 ml of aqueous sodium carbonate (1M), followed by 100 mg of dichlorobis-(triphenylphosphine)-palladium(II). The reaction vessel was sealed and heated at 150° C. for 5 minutes with microwave irradiation. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was evaporated to provide a crude material, which was purified by ISCO to give 220 mg of 2-pyrimidin-5-yl-benzaldehyde.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with ethylacetate
  4. customThe organic layer was evaporated
  5. customto provide a crude material, which
  6. customwas purified by ISCO

Sources & evidence

ORD record
ord-c9b8b8f8c98042a2aff09f4ff72375c4
Source dataset
uspto-grants-2009_06
Patent number
US07553840B2

Reaction notes

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