Water → 4-(4,4-Dimethyl-2-pentynyloxy)-6-(2,3-difluorophenyl)pyrimidine

HRID 1759907Notes

Reaction equation

HRID 1759907 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[F:15])[N:5]=[CH:4][N:3]=1.[CH3:16][C:17]([CH3:23])([CH3:22])[C:18]#[C:19][CH2:20][OH:21].[H-].[Na+].O>CN(C)C=O>[CH3:16][C:17]([CH3:23])([CH3:22])[C:18]#[C:19][CH2:20][O:21][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[F:15])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 117891624,4-Dimethylpent-2-yn-1-olHCID 225997504-Chloro-6-(2,3-difluorophenyl)pyrimidine

Product 1

HCID 225998264-(4,4-Dimethyl-2-pentynyloxy)-6-(2,3-difluorophenyl)pyrimidineYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 6 ml of N,N-dimethylformamide were dissolved 199 mg of 4-chloro-6-(2,3-difluorophenyl)pyrimidine and 118 mg of 4,4-dimethyl-2-pentyn-1-ol, to which 43 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 3 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 190 mg of 4-(4,4-dimethyl-2-pentynyloxy)-6-(2,3-difluorophenyl)pyrimidine (the present compound (119)).

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-8b2dbd73456d478cbb363703c9225fb1
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

Loading…