Pyridine → 2,2,2-Trichloroethyl [2-(acetylamino)pyrimidin-5-yl]carbamate
Reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.N1C=CC=CC=1.Cl[C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20]>O1CCCC1>[C:9]([NH:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:19](=[O:20])[O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[CH:3][N:4]=1)(=[O:11])[CH3:10]Participants
5
Procedure
To a solution of N-(5-aminopyrimidin-2-yl)acetamide (450 mg, 2.96 mmol) and pyridine (0.718 ml, 8.87 mmol) in tetrahydrofuran (10 ml) was added 2,2,2-trichloroethyl chloroformate (0.612 ml, 4.44 mmol) with ice-cooling, the mixture was stirred for 1 hour with ice-cooling and then at room temperature for 2 hours, the reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to obtain the desired product (88.3 mg, 9.1%) as a solid.
Workup
- temperaturecooling
- temperaturecooling
- waitat room temperature for 2 hours
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-5a2bd0324af9492eb9f6340a258a7f9f
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851473B2
Reaction notes
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