2,2,2-Trifluoroethanol → HCID 19392531, compound

HRID 491270Notes

Reaction equation

HRID 491270 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[Cl:9][C:10]1[N:15]=[C:14](Cl)[CH:13]=[CH:12][N:11]=1>CN(C=O)C.O>[Cl:9][C:10]1[N:15]=[C:14]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 775312,4-Dichloropyrimidine

Product 1

HCID 19392531HCID 19392531, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride/60 percent oil dispersion (286 mg, 7.1 mmol) in DMF (10 mL) was added 2,2,2-trifluoroethanol (675 mg, 6.7 mmol). The reaction mixture was stirred for 30 minutes, then it was then added dropwise over 30 minutes to a solution of 2,4-dichloropyrimidine (1.0 g, 6.7 mmol). The solution was then allowed to stir overnight while warming to room temperature. The solution was diluted with H2O and extracted thrice with Et2O. The organics were combined, washed with brine, dried (Na2SO4) and filtered through silica gel, eluting with ether. The product was isolated as a semi-solid, 1.1 g, 5.2 mmol, 78 percent yield.

Workup

  1. stirringto stir overnight
  2. extractionextracted thrice with Et2O
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered through silica gel
  6. washeluting with ether
  7. customThe product was isolated as a semi-solid, 1.1 g, 5.2 mmol, 78 percent yield

Sources & evidence

ORD record
ord-8302aaad4b43451d9e75a34c672bd6ba
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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