Dimethylformamide → 4-(2-Butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine
Reaction equation
CN(C)C=O.[CH2:6]([O:10][C:11]1[C:16]([F:17])=[C:15](Cl)[N:14]=[CH:13][N:12]=1)[C:7]#[C:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].[CH3:25][C:26]1([CH3:31])[CH2:30][CH2:29][NH:28][CH2:27]1>C(OCC)(=O)C>[CH2:6]([O:10][C:11]1[C:16]([F:17])=[C:15]([N:28]2[CH2:29][CH2:30][C:26]([CH3:31])([CH3:25])[CH2:27]2)[N:14]=[CH:13][N:12]=1)[C:7]#[C:8][CH3:9]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Into 4 ml of N,N-dimethylformamide was resolved 0.36 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine, 0.62 g of potassium carbonate and 0.25 g of 3,3-dimethylpyrrolidine was added therein, and the mixture was stirred for 6 hours at 80° C. The reaction mixture was cooled to near room temperature, ethyl acetate was added therein, and the mixture was washed with a saturated sodium chloride aqueous solution three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.15 g of 4-(2-butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine (hereinafter, referred to as Compound (28)).
Workup
- additionwas added
- temperatureThe reaction mixture was cooled to near room temperature
- washthe mixture was washed with a saturated sodium chloride aqueous solution three times
- dry with materialThe organic layers were dried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c9309cc34ae84269932079798988a296
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732448B2
Reaction notes
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