Potassium Carbonate → HCID 66594974, compound
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[C:11][CH3:12])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:20][C@H:21]1[CH2:26][C@@H:25]([CH3:27])[CH2:24][NH:23][CH2:22]1.[Cl-].[NH4+]>CN(C)C=O>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([N:23]2[CH2:24][C@H:25]([CH3:27])[CH2:26][C@H:21]([CH3:20])[CH2:22]2)[N:3]=[CH:4][N:5]=1)[C:10]#[C:11][CH3:12]Participants
Conditions
- Temperature
- 70 °C
Procedure
Into 3 ml of N,N-dimethylformamide was resolved 0.3 g of 4-chloro-6-(2-butynyloxy)pyrimidine, 0.57 g of potassium carbonate and 0.25 g of cis-3,5-dimethylpiperidine hydrochloride was added therein, and the mixture was stirred for 40 minutes 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 three times. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.41 g of 4-(2-butynyloxy)-6-(cis-3,5-dimethylpiperidino)pyrimidine (hereinafter, referred to as Compound (23)).
Workup
- additionwas added
- 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 three times
- dry with materialThe organic layers were dried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4c12d0d83f2640f9a977c9ffd5d264a0
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968537B2
Reaction notes
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