1,2-Dimethoxyethane → 4-Chloro-6-(4-fluorophenyl)pyrimidine

HRID 1759961Notes

Reaction equation

HRID 1759961 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.COCCOC.[Cl:17][C:18]1[CH:23]=[C:22](Cl)[N:21]=[CH:20][N:19]=1>O>[Cl:17][C:18]1[CH:23]=[C:22]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:21]=[CH:20][N:19]=1

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 709434,6-DichloropyrimidineHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 5997284-Chloro-6-(4-fluorophenyl)pyrimidineYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A reaction vessel was charged with 0.255 g of tetrakistriphenylphosphine palladium, 1.132 g of 4-fluorophenylboronic acid, and 3.122 g of tripotassium phosphate n-hydrate, to which 36 ml of 1,2-dimethoxyethane, 9 ml of water, and 1.095 g of 4,6-dichloropyrimidine were added, followed by stirring at 80° C. under an atmosphere of a nitrogen gas for 8 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 0.399 g of 4-chloro-6-(4-fluorophenyl)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-6890b28ec0e949f7a7ca882ef46d7105
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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