Water → HCID 22599847, compound

HRID 1759848Notes

Reaction equation

HRID 1759848 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH2:15]([OH:19])[C:16]#[C:17][CH3:18].[H-].[Na+].O>CN(C)C=O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:7]=[C:2]([O:19][CH2:15][C:16]#[C:17][CH3:18])[N:3]=[CH:4][N:5]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 5997284-Chloro-6-(4-fluorophenyl)pyrimidine

Product 1

HCID 22599847HCID 22599847, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 8 ml of N,N-dimethylformamide were dissolved 207 mg of 4-chloro-6-(4-fluorophenyl)pyrimidine and 83 mg of 2-butyn-1-ol, to which 48 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 9 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 138 mg of 4-(4-fluorophenyl)-6-(2-butynyloxy)pyrimidine (the present compound (59)).

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-844408afc9df445db543508a27b01f4c
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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