Water → 4-Chloro-6-[2,2,2-trifluoro-1-(2-furan-3-yl-phenyl)-ethoxy]-pyrimidine

HRID 1988061Notes

Reaction equation

HRID 1988061 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[CH:17]=[CH:16][O:15][CH:14]=1)[OH:6].[Cl:20][C:21]1[CH:26]=[C:25](Cl)[N:24]=[CH:23][N:22]=1.O>C1COCC1>[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[CH:17]=[CH:16][O:15][CH:14]=2)[C:4]([F:3])([F:18])[F:19])[N:24]=[CH:23][N:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 709434,6-DichloropyrimidineHCID 667436882,2,2-Trifluoro-1-(2-furan-3-yl-phenyl)-ethanol

Product 1

HCID 866210994-Chloro-6-[2,2,2-trifluoro-1-(2-furan-3-yl-phenyl)-ethoxy]-pyrimidineYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Sixty percent NaH (12 mg, 0.3 mmol) was added to a solution of 2,2,2-trifluoro-1-(2-furan-3-yl-phenyl)-ethanol (54 mg, 0.2 mmol) in 10 ml of anhydrous THF. The mixture was stirred for 20 minutes, after which 4,6-dichloro-pyrimidine (30 mg, 0.2 mmol) was added. The mixture was then heated at 70° C. until the reaction was complete. After cooling, 5 ml of water was added to quench the reaction, 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 of 67 mg 4-chloro-6-[2,2,2-trifluoro-1-(2-furan-3-yl-phenyl)-ethoxy]-pyrimidine (yield: 94%).

Workup

  1. temperatureAfter cooling
  2. customto quench
  3. customthe reaction, and ethyl acetate (20 ml)
  4. extractionto extract the product
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customThe solvent was removed by rotovap

Sources & evidence

ORD record
ord-155a062ca06f457e8b08a8fad09950d2
Source dataset
uspto-grants-2009_06
Patent number
US07553840B2

Reaction notes

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