Sodium hydride → HCID 86698875, compound

HRID 339930Notes

Reaction equation

HRID 339930 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][N:5]=[CH:4][N:3]=1.[F:15][C:16]([F:26])([F:25])[C:17]1[CH:24]=[CH:23][C:20]([CH2:21][OH:22])=[CH:19][CH:18]=1.[H-].[Na+]>CC(N(C)C)=O>[F:15][C:16]([F:25])([F:26])[C:17]1[CH:24]=[CH:23][C:20]([CH2:21][O:22][C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:6][N:5]=[CH:4][N:3]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 676844-(Trifluoromethyl)benzenemethanolHCID 21557075HCID 21557075, compound

Product 1

HCID 86698875HCID 86698875, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-chloro-5-phenoxypyrimidine (0.4 g, 1.9 mmol) described in JP-A-49-92080 and 4-trifluoromethylbenzylalcohol (0.36 g, 2.0 mmol) in dimethylacetamide (7 m) was added sodium hydride (0.093 g, 2.3 mmol) at 0° C., and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 4-(4-trifluoromethylbenzyloxy)-5-phenoxypyrimidine (0.60 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-51e9ec9cda2a4995aa70de870b2f18e0
Source dataset
uspto-grants-2014_11
Patent number
US08895574B2

Reaction notes

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