Potassium Carbonate → 2-Chloro-5-(4-fluorophenyl)pyrimidine

HRID 500112Notes

Reaction equation

HRID 500112 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:8][C:5]1[N:4]=[CH:3][C:2]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 203333512-Chloro-5-(4-fluorophenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5-bromo-2-chloropyrimidine (500 mg, 2 mmol), 4-fluorophenylboronic acid (430 mg, 3.1 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (210 mg, 0.26 mmol) and potassium carbonate (1.8 g, 13 mmol) in 1,4-dioxane (6 mL) was irradiated under microwave at 120° C. for 30 min. After cooling, the solvent was evaporated. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes to give the desired product. (376 mg) LCMS: (M+H)=209.0.

Workup

  1. customwas irradiated under microwave at 120° C. for 30 min
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. customThe residue was purified by flash chromatography
  5. washeluting with ethyl acetate in hexanes

Sources & evidence

ORD record
ord-96cd4049b0794d2f9e6e52cab26169f1
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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