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

HRID 1759906Notes

Reaction equation

HRID 1759906 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[F:15])[N:5]=[CH:4][N:3]=1.[CH2:16]([OH:22])[C:17]#[C:18][CH2:19][CH2:20][CH3:21].[H-].[Na+].O>CN(C)C=O>[F:15][C:9]1[C:10]([F:14])=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[CH:7]=[C:2]([O:22][CH2:16][C:17]#[C:18][CH2:19][CH2:20][CH3:21])[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69818Hex-2-yn-1-olHCID 225997504-Chloro-6-(2,3-difluorophenyl)pyrimidine

Product 1

HCID 225996874-(2,3-Difluorophenyl)-6-(2-hexynyloxy)pyrimidineYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 9 ml of N,N-dimethylformamide were dissolved 217 mg of 4-chloro-6-(2,3-difluorophenyl)pyrimidine and 141 mg of 2-hexyn-1-ol, to which 58 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 7 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 247 mg of 4-(2,3-difluorophenyl)-6-(2-hexynyloxy)pyrimidine (the present compound (118)).

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-7fba6ccfdadc42a4ba12e10a8b0c287d
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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