Water → (1S)-5-(1-Methyl-6-oxo-4-pyridin-4-yl-1,6-dihydro-pyrimidin-2-yl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
Reaction equation
C(N(CC)CC)C.Cl.Cl[C:10]1[N:15]([CH3:16])[C:14](=[O:17])[CH:13]=[C:12]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:11]=1.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH:35]2[CH2:37][C@H:32]1[CH2:33][NH:34]2)=[O:30])([CH3:27])([CH3:26])[CH3:25].O>CN(C)C=O>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH:35]2[CH2:37][C@H:32]1[CH2:33][N:34]2[C:10]1[N:15]([CH3:16])[C:14](=[O:17])[CH:13]=[C:12]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[N:11]=1)=[O:30])([CH3:27])([CH3:25])[CH3:26]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A mixture containing 10.7 ml (78.14 mmol) of triethylamine, 13.6 g (52.7 mmol) of 2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one hydrochloride (1:1), 6.0 g (30.24 mmol) of (1S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester in 500 ml of anhydrous dimethylformamide is stirred at 20° C. for 6 h. Water is added to the cooled mixture and the resulting solution extracted with ethyl acetate. The combined extracts are washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride then-evaporated. The crude product is refluxed in diethylether for 1 h to afford 8.36 g of pure product as a brown solid.
Workup
- extractionthe resulting solution extracted with ethyl acetate
- washThe combined extracts are washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
- customthen-evaporated
- temperatureThe crude product is refluxed in diethylether for 1 h
Sources & evidence
- ORD record
- ord-0c65aa05e37f49ecb6cd4748622a6d81
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211581B2
Reaction notes
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