Carbon Dioxide → HCID 21935657, compound
Reaction equation
CC(C[AlH]CC(C)C)C.C(=O)=O.C[O:14][C:15]([C:17]1[C:18]([CH2:33][CH2:34][O:35][CH3:36])=[N:19][C:20]([C:23]2[CH:24]=[N:25][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:28]=2)=[N:21][CH:22]=1)=O.C(OC(C1C(CCOC)=NC(C2C=NC(C(F)(F)F)=CC=2)=NC=1)=O)C.OS([O-])(=O)=O.[K+]>C1COCC1>[CH3:36][O:35][CH2:34][CH2:33][C:18]1[C:17]([CH2:15][OH:14])=[CH:22][N:21]=[C:20]([C:23]2[CH:24]=[N:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=2)[N:19]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Within 20 min was dropped 50 ml (60 mmol) of DIBALH (1.2 M solution in toluene) to a dry ice cooled (−30° C.) solution of 6.83 g (20 mmol) 4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine-5-carboxylic acid methyl ester and 4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidine-5-carboxylic acid ethyl ester in 100 ml of THF. The reaction was warmed up (0° C. for 1 h) and stirred 1 h at RT. The reaction was cooled (0° C.) and neutralized with KHSO4 solution (10%). 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 crystallized (dichloromethane/ether, 0° C.) to give 6.72 g of pure [4-(2-methoxy-ethyl)-2-(6-trifluoromethyl-pyridin-3-yl)-pyrimidin-5-yl]-methanol.
Workup
- temperatureThe reaction was cooled (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 crystallized (dichloromethane/ether, 0° C.)
Sources & evidence
- ORD record
- ord-bfeb831a9fe94004ac68a668b652fdaf
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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