Dimethylformamide → HCID 86682473, compound

HRID 632619Notes

Reaction equation

HRID 632619 reaction equation
CN(C)C=O.Br[C:7]1[CH:8]=[N:9][C:10]([Cl:13])=[N:11][CH:12]=1.[CH3:14][O:15][C:16]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:13][C:10]1[N:9]=[CH:8][C:7]([C:22]2[CH:23]=[C:18]([CH:19]=[CH:20][CH:21]=2)[C:16]([O:15][CH3:14])=[O:17])=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 27347143-(Methoxycarbonyl)benzeneboronic acid

Product 1

HCID 86682473HCID 86682473, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To 2 ml of N,N-dimethylformamide deaerated with argon for 10 minutes, 213 mg (1.10 mmol) of 5-bromo-2-chloropyrimidine, 181 mg (1.05 mmol) of 3-(methoxycarbonyl)phenylboronic acid, 315 mg (2.97 mmol) of sodium carbonate and 22.4 mg (0.100 mmol) of palladium acetate were added, and the mixture was stirred at 110° C. for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with toluene three times. The obtained organic phases were combined, washed with saturated sodium chloride aqueous solution, dried with magnesium sulfate and then filtered, and the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=92/8-76/24 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 74 mg of the title compound as a white solid (yield: 28%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with toluene three times
  3. washwashed with saturated sodium chloride aqueous solution
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. distillationthe solvent was distilled off under reduced pressure
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-51b49a2cc5904681a7e0b127d9a4d18f
Source dataset
uspto-grants-2016_04
Patent number
US09321747B2

Reaction notes

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