Water → 4-(2,3-Difluorophenyl)-6-(3-chloro-2-propynyloxy)pyrimidine

HRID 1592197Notes

Reaction equation

HRID 1592197 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]#[CH:18])[N:12]=[CH:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+].O.C(Cl)(Cl)(Cl)[Cl:27]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]#[C:18][Cl:27])[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 11430Potassium CarbonateHCID 225998534-(2,3-Difluorophenyl)-6-(2-propynyloxy)pyrimidine

Product 1

HCID 225998304-(2,3-Difluorophenyl)-6-(3-chloro-2-propynyloxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

In 5 ml of carbon tetrachloride was dissolved 241 mg of 4-(2,3-difluorophenyl)-6-(2-propynyloxy)pyrimidine, to which 136 mg of potassium carbonate and 136 mg of tetra-n-butylammonium chloride were added, followed by stirring at room temperature for 16 hours. The reaction mixture was then poured into water and 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 resulting residue was subjected to silica gel column chromatography to give 159 mg of 4-(2,3-difluorophenyl)-6-(3-chloro-2-propynyloxy)pyrimidine (the present compound (136)).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a3de8785b3dc4116b9d5ca5bbc4cd632
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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