Dimethylformamide → HCID 22599852, compound
Reaction equation
CN(C)C=O.Cl[C:7]1[CH:12]=[C:11]([O:13][CH2:14][C:15]#[C:16][CH3:17])[N:10]=[CH:9][N:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25]>C(OCC)(=O)C>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]([N:26]([CH2:27][CH3:28])[CH2:24][CH3:25])[N:8]=[CH:9][N:10]=1)[C:15]#[C:16][CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To 2 ml of N,N-dimethylformamide were added 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate, and 73 mg of diethylamine, followed by stirring at a bath temperature of 50° C. for 4 hours. Then, 73 mg of diethylamine was further added, followed by stirring at a bath temperature of 50° C. for 5.5 hours. Then, 146 mg of diethylamine was further added, followed by stirring at a bath temperature of 40° C. for 6 hours. The reaction mixture was left for cooling to room temperature, diluted with ethyl acetate, and washed three times with an aqueous sodium chloride solution. The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel thin layer chromatography to give 136 mg of 4-(2-butynyloxy)-6-(N,N-diethylamino)pyrimidine (the present compound (144)).
Workup
- stirringby stirring at a bath temperature of 50° C. for 5.5 hours
- stirringby stirring at a bath temperature of 40° C. for 6 hours
- waitThe reaction mixture was left
- temperaturefor cooling to room temperature
- washwashed three times with an aqueous sodium chloride solution
- dry with materialThe organic layers were dried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1d79aee19a2944ab81db57fee0b98fde
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291730B2
Reaction notes
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