Carbon Dioxide → [4-Trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol
Reaction equation
CC(C[AlH]CC(C)C)C.C(=O)=O.C([O:15][C:16]([C:18]1[C:19]([C:34]([F:37])([F:36])[F:35])=[N:20][C:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[N:22][CH:23]=1)=O)C.C([O-])(O)=O.[Na+]>C1COCC1>[F:37][C:34]([F:35])([F:36])[C:19]1[C:18]([CH2:16][OH:15])=[CH:23][N:22]=[C:21]([C:24]2[CH:25]=[CH:26][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:28][CH:29]=2)[N:20]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
Within 10 min was dropped 5.5 ml (6.6 mmol) of DIBALH (1.2 M solution in toluene) to a dry ice cooled (−30° C.) solution of 1.09 g (3.0 mmol) 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid ethyl ester in 15 ml of THF. The reaction was stirred for 2.5 h at −30° C., warmed up (0° C. for 2 h) and stirred 1 h at 0° C. The reaction was neutralized with saturated NaHCO3 solution. The mixture was extracted with ether (3×), the organic phase was washed with a NaCl solution (10%), dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography over silica gel with heptane/isopropanol 9:1, to give 0.16 g of pure [4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol as a yellow solid.
Workup
- temperaturewarmed up (0° C. for 2 h)
- stirringstirred 1 h at 0° C
- extractionThe mixture was extracted with ether (3×)
- washthe organic phase was washed with a NaCl solution (10%)
- dry with materialdried (Na2SO4)
- customevaporated
- customThe crude product was purified by flash chromatography over silica gel with heptane/isopropanol 9:1
Sources & evidence
- ORD record
- ord-78bfa358dc9a4f3aa2c9c2cdb13bffa5
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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