Water → 4-(2-Fluorophenyl)-6-(4-hydroxy-2-butynyloxy)pyrimidine

HRID 1759990Notes

Reaction equation

HRID 1759990 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:5]=[CH:4][N:3]=1.[CH2:15]([OH:20])[C:16]#[C:17][CH2:18][OH:19].[H-].[Na+].O>CN(C)C=O>[F:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[CH:7]=[C:2]([O:19][CH2:18][C:17]#[C:16][CH2:15][OH:20])[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 80662-Butyne-1,4-diolHCID 24758Sodium hydrideHCID 225998154-Chloro-6-(2-fluorophenyl)pyrimidine

Product 1

HCID 225997694-(2-Fluorophenyl)-6-(4-hydroxy-2-butynyloxy)pyrimidineYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of N,N-dimethylformamide were dissolved 608 mg of 4-chloro-6-(2-fluorophenyl)pyrimidine and 527 mg of 2-butyn-1,4-diol, to which 245 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 465 mg of 4-(2-fluorophenyl)-6-(4-hydroxy-2-butynyloxy)pyrimidine.

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-e85c944a4b8644cf9a15b39d1e9ebca5
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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