1,2-Dimethoxyethane → HCID 22599699, compound

HRID 1759974Notes

Reaction equation

HRID 1759974 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1B(O)O.COCCOC.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=1>O>[Cl:18][C:19]1[CH:24]=[C:23]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[F:8])[N:22]=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 709434,6-DichloropyrimidineHCID 27343362,6-Difluorophenylboronic acid

Product 1

HCID 22599699HCID 22599699, compoundYield 16.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A reaction vessel was charged with [1,1′-bis(diphenylphosphino)ferrocene dichloropalladium]methylene chloride complex, 1.007 g of 2,6-difluorophenylboronic acid, and 2.707 g of tripotassium phosphate n-hydrate, to which 16 ml of 1,2-dimethoxyethane, 4 ml of water, and 0.95 g of 4,6-dichloropyrimidine were added, followed by stirring at 80° C. under an atmosphere of a nitrogen gas for 5 hours. The reaction mixture was then left for cooling to room temperature, and water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.241 g of 4-chloro-6-(2,6-difluorophenyl)pyrimidine.

Workup

  1. additionwere added
  2. waitThe reaction mixture was then left
  3. temperaturefor cooling to room temperature
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a46882e1af134ad08e69b4b3160ec7db
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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