Water → 4-(2-Fluorophenyl)-6-(3-butynyloxy)pyrimidine

HRID 1759930Notes

Reaction equation

HRID 1759930 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:19])[CH2:16][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][CH2:15][CH2:16][C:17]#[CH:18])[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 135663-Butyn-1-OLHCID 24758Sodium hydrideHCID 225998154-Chloro-6-(2-fluorophenyl)pyrimidine

Product 1

HCID 225997994-(2-Fluorophenyl)-6-(3-butynyloxy)pyrimidineYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of N,N-dimethylformamide were dissolved 450 mg of 4-chloro-6-(2-fluorophenyl)pyrimidine and 227 mg of 3-butyn-1-ol, to which 130 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 12 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 302 mg of 4-(2-fluorophenyl)-6-(3-butynyloxy)pyrimidine (the present compound (152)).

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-7d0d86061ab4407d911af88d9a55c02f
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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