Water → 4-(2-Fluorophenyl)-6-(1-methyl-2-propynyloxy)pyrimidine

HRID 1759928Notes

Reaction equation

HRID 1759928 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.[CH3:15][CH:16]([OH:19])[C:17]#[CH:18].[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][CH:16]([CH3:15])[C:17]#[CH:18])[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 162393-Butyn-2-olHCID 24758Sodium hydrideHCID 225998154-Chloro-6-(2-fluorophenyl)pyrimidine

Product 1

HCID 225997674-(2-Fluorophenyl)-6-(1-methyl-2-propynyloxy)pyrimidineYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of N,N-dimethylformamide were dissolved 458 mg of 4-chloro-6-(2-fluorophenyl)pyrimidine and 231 mg of 3-butyn-2-ol, to which 132 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 10 hours. The reaction mixture was then poured into water and extracted three times with ethyl acetate. The organic layers were combined, 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 506 mg of 4-(2-fluorophenyl)-6-(1-methyl-2-propynyloxy)pyrimidine (the present compound (150)).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-541ac06aff9e46da8d77d41855e8eab4
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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