Potassium Carbonate → 4-(2-Butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidin-1-yl)pyrimidine
Reaction equation
[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10](F)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].Cl.[CH3:15][C:16]1([CH3:21])[CH2:20][CH2:19][NH:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(#N)C>[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10]([N:18]2[CH2:19][CH2:20][C:16]([CH3:21])([CH3:15])[CH2:17]2)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
0.36 g of 4-(2-butynyloxy)-5,6-difluoropyrimidine, 0.25 g of 3,3-dimethylpyrrolidine hydrochloride and 0.62 g of potassium carbonate are added to 1 ml of acetonitrile, then the reaction mixture is stirred at 70° C. for 5 hours. Then saturated aqueous solution of ammonium chloride is added to the reaction mixture which is cooled to about room temperature, and extract with t-butyl methyl ether three times. The organic layers are joined, dried with anhydrous magnesium sulfate, and concentrated. The residue is subjected to silica gel column chromatography to obtain 4-(2-butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidine-1-yl)pyrimidine (referred as the present compound (8) hereinafter).
Workup
- temperatureis cooled to about room temperature
- extractionextract with t-butyl methyl ether three times
- dry with materialdried with anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8456e423dfda4991a67bb009dd26559a
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101753B2
Reaction notes
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