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

HRID 1592149Notes

Reaction equation

HRID 1592149 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:19])[C:17]#[CH:18].[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:19][CH2:16][C:17]#[CH:18])[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 225997504-Chloro-6-(2,3-difluorophenyl)pyrimidine

Product 1

HCID 225998534-(2,3-Difluorophenyl)-6-(2-propynyloxy)pyrimidineYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 6 ml of N,N-dimethylformamide were dissolved 96 mg of 4-chloro-6-(2,3-difluorophenyl)pyrimidine and 26 mg of 2-propyn-1-ol, to which 19 mg of sodium hydride. (60% in oil) was added, followed by stirring at room temperature for 8 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 42 mg of 4-(2,3-difluorophenyl)-6-(2-propynyloxy)pyrimidine (the present compound (82)).

Workup

  1. addition(60% in oil) was added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c855f954681492fb9db58b8d2256e4e
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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