Potassium Carbonate → Pyrimidin-4-yl-5,6,8,9-tetrahydro-7-oxa-1,4a-diaza-benzocyclohepten-4-one
Reaction equation
Cl.[O:2]1[CH2:8][CH2:7][C:6]([NH2:9])=[N:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[N:16]1[CH:21]=[CH:20][C:19]([C:22](=O)[CH2:23][C:24](OCC)=[O:25])=[N:18][CH:17]=1>C(O)C>[N:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:9]=[C:6]3[CH2:7][CH2:8][O:2][CH2:3][CH2:4][N:5]3[C:24](=[O:25])[CH:23]=2)=[N:18][CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 25.00 g (165.99 mmol) of 2,3,6,7-tetrahydro-[1,4]oxazepin-5-ylamine monohydrochloride (synthesis as described in WO97/16430 and Bioorganic & Medicinal Chemistry Letters (2004), 14(23), 5907-5911) in 550 mL of ethanol was added 25.23 g (182.59 mmol) of potassium carbonate. The reaction mixture was stirred at room temperature for 10 min, 35.45 g (182.59 mmol) of ethyl 3-(4-pyrimidinyl)-3-oxopropionate was added and the resulting mixture was stirred under reflux for 4 hours. The cooled solution was evaporated to remove solvent. The mixture was dissolved with water and diethyl ether. After stirring, the resulting solid was filtered, washed with water and diethyl ether to afford 21.7 g (53%) of the desired compound as a powder.
Workup
- customsynthesis
- stirringthe resulting mixture was stirred
- temperatureunder reflux for 4 hours
- customThe cooled solution was evaporated
- customto remove solvent
- dissolutionThe mixture was dissolved with water and diethyl ether
- stirringAfter stirring
- filtrationthe resulting solid was filtered
- washwashed with water and diethyl ether
Sources & evidence
- ORD record
- ord-34efcbcdf2a04708aed7be3836360bdb
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501728B2
Reaction notes
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