Water → HCID 86621100, compound

HRID 1620873Notes

Reaction equation

HRID 1620873 reaction equation
[H-].[Na+].[F:3][C:4]([F:19])([F:18])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[OH:6].[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[CH:23][N:22]=1.O>C1COCC1.C(OCC)(=O)C>[Cl:20][C:21]1[CH:26]=[C:25]([O:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:4]([F:3])([F:18])[F:19])[N:24]=[CH:23][N:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 66743675HCID 66743675, compound

Product 1

HCID 86621100HCID 86621100, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Sixty percent NaH (12 mg, 0.3 mmol) was added to a solution of 2,2,2-trifluoro-1-(2-furan-2-yl-phenyl)-ethanol (55 mg, 0.2 mmol) in 10 ml of anhydrous THF. The mixture was stirred for 20 minutes, after which 4,6-dichloro-pyrimidine (29 mg, 0.2 mmol) was added. The mixture was then heated at 110° C. until the reaction was complete. After cooling, 5 ml of water was added, and ethyl acetate (20 ml) was used to extract the product. The organic layer was dried over sodium sulfate. The solvent was removed by rotovap to give 60 mg of 4-chloro-6-[2,2,2-trifluoro-1-(2-furan-2-yl-phenyl)-ethoxy]-pyrimidine (yield 80%).

Workup

  1. temperatureAfter cooling
  2. extractionto extract the product
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe solvent was removed by rotovap

Sources & evidence

ORD record
ord-a20d3e9d444e4fc4b5e9816baa7656de
Source dataset
uspto-grants-2014_07
Patent number
US08772482B2

Reaction notes

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