Water → 4-(3-Fluorophenyl)-6-(1-methyl-2-butynyloxy)pyrimidine

HRID 1592224Notes

Reaction equation

HRID 1592224 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH3:15][CH:16]([OH:20])[C:17]#[C:18][CH3:19].[H-].[Na+].O>CN(C)C=O>[F:14][C:10]1[CH:9]=[C:8]([C:6]2[CH:7]=[C:2]([O:20][CH:16]([CH3:15])[C:17]#[C:18][CH3:19])[N:3]=[CH:4][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1413443-Pentyn-2-olHCID 6103714-Chloro-6-(3-fluorophenyl)pyrimidine

Product 1

HCID 225998224-(3-Fluorophenyl)-6-(1-methyl-2-butynyloxy)pyrimidineYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 5 ml of N,N-dimethylformamide were dissolved 246 mg of 4-chloro-6-(3-fluorophenyl)pyrimidine and 119 mg of 3-pentyn-2-ol, to which 57 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 200 mg of 4-(3-fluorophenyl)-6-(1-methyl-2-butynyloxy)pyrimidine (the present compound (173)).

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-050567cc3ea74fd0b53870a61098a7fa
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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