Potassium Carbonate → 4-(2-Butynyloxy)-6-(3,4-dimethylpyrrolidin-1-yl)pyrimidine
Reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10](Cl)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:20][CH:21]1[CH:25]([CH3:26])[CH2:24][NH:23][CH2:22]1.[Cl-].[NH4+]>C(#N)C>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([N:23]2[CH2:24][CH:25]([CH3:26])[CH:21]([CH3:20])[CH2:22]2)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
Into 3 ml of acetonitrile were added 0.30 g of 4-(2-butynyloxy)-6-chloropyrimidine, 0.68 g of potassium carbonate and 0.33 g of 3,4-dimethylpyrrolidine hydrochloride (cis and trans diastereomer mixture), and the mixture was stirred for 4 hours at 70° C. The reaction mixture was cooled to near room temperature, a saturated ammonium chloride aqueous solution was added therein, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.42 g of 4-(2-butynyloxy)-6-(3,4-dimethylpyrrolidin-1-yl)pyrimidine (hereinafter, referred to as Compound (37)).
Workup
- temperatureThe reaction mixture was cooled to near room temperature
- extractionthe mixture was extracted with tert-butyl methyl ether three times
- washThe organic layers were washed with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f58d1c350c6040e9aa051c2443a078bd
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973028B2
Reaction notes
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