Sodium Carbonate → 5-(4-Formylphenyl)pyrimidine

HRID 643086Notes

Reaction equation

HRID 643086 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH:14]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)=[O:15]>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:4]1[CH:3]=[C:2]([C:19]2[CH:18]=[CH:17][C:16]([CH:14]=[O:15])=[CH:21][CH:20]=2)[CH:7]=[N:6][CH:5]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 783445-BromopyrimidineHCID 27343563-Formylphenylboronic acid

Product 1

HCID 38612125-(4-Formylphenyl)pyrimidineYield 60%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromopyrimidine (159 mg, 1 mmol) was dissolved in toluene (5 mL) and treated with tetrakis(triphenylphosphine)-palladium(0) (116 mg, 0.1 equivalent) and a 2 M solution of sodium carbonate (1 mL, 2 equivalents). The mixture was stirred under an argon atmosphere for 20 min. followed by addition of 3-formylphenyl boronic acid (165 mg, 1.1 equivalensts) in ethanol (1 mL). The reaction was heated to 80° C. and stirred for 16 hrs. The mixture was filtered and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and the solvent was removed by evaporation. This material was purified using hexanes:dichloromethane (1:1) followed by dichloromethane:methanol (97:3) to give 110 mg (60%) of the title compound.

Workup

  1. stirringstirred for 16 hrs
  2. filtrationThe mixture was filtered
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed by evaporation
  8. customThis material was purified

Sources & evidence

ORD record
ord-9d7b8150142942b3b893c1e08d6dbfe7
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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