2,2,2-Trifluoroethanol → HCID 86663137, compound

HRID 1528362Notes

Reaction equation

HRID 1528362 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].[Cl:9][C:10]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:13](F)=[CH:12][N:11]=1>CN(C=O)C>[Cl:9][C:10]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[C:13]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 79073067HCID 79073067, compound

Product 1

HCID 86663137HCID 86663137, compoundYield 61.81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 2.0 ml 2,2,2-trifluoroethanol in 35 mL dry DMF was added 1.1 g sodium hydride was added and the mixture was stirred at room temperature for 15 minutes. The resulting solution was added drop wise at −10° C. to a solution of 7 g 2-chloro-4-(3,4-dichloro-phenyl)-5-fluoro-pyrimidine in 50 mL dry DMF during 39 min. The reaction mixture was then stirred at room temperature for 2 h. The resulting brown mixture was partitioned between water and ethyl acetate, the phases were separated the organic phase was dried over MgSO4 and purified by chromatography on silica gel with a gradient of heptane:dichloromethane=1:1 to dichloromethane to yield 5.575 g (61.81%) of the title compound as light yellow solid, MS 356.9 (M+H)+.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was then stirred at room temperature for 2 h
  3. customThe resulting brown mixture was partitioned between water and ethyl acetate
  4. customthe phases were separated the organic phase
  5. dry with materialwas dried over MgSO4
  6. custompurified by chromatography on silica gel with a gradient of heptane

Sources & evidence

ORD record
ord-22e42c1b3a9a454e90a0a470e386bece
Source dataset
uspto-grants-2015_07
Patent number
US09090599B2

Reaction notes

Loading…