Carbon Dioxide → 4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carbaldehyde
Reaction equation
C(=O)=O.CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH:14]1([C:17]2[C:22]([CH2:23][OH:24])=[CH:21][N:20]=[C:19]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[N:18]=2)[CH2:16][CH2:15]1.C(N(CC)CC)C>ClCCl.CCOCC>[CH:14]1([C:17]2[C:22]([CH:23]=[O:24])=[CH:21][N:20]=[C:19]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][CH:26]=3)[N:18]=2)[CH2:16][CH2:15]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -70 °C
Procedure
To a dry ice cooled solution of 0.86 ml (12 mmol) DMSO in 10 ml dichloromethane was added 0.68 ml (7.79 mmol) oxalylchloride. After the reaction mixture was stirred for 5 min at −70° C., 1.8 g (5.99 mmol) of [4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol, dissolved in 8 ml dichloromethane, was added by dropping within 5 min. The reaction mixture was then stirred for further ten minutes at −70° C. and after 4.17 ml (30 mmol) triethylamine was added, the reaction mixture was allowed to come to RT and it was stirred for 1 h at RT. The mixture was taken up in ether and washed with 1N HCl and water. The ether phase was concentrated under reduced pressure to give 1.75 g of pure 4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carbaldehyde.
Workup
- additionwas added
- waitby dropping within 5 min
- stirringThe reaction mixture was then stirred for further ten minutes at −70° C.
- customto come to RT
- stirringit was stirred for 1 h at RT
- washwashed with 1N HCl and water
- concentrationThe ether phase was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-885ba874ceff49ed85e7e706ce324622
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
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