Einecs 211-027-4 → ethyl 3-cyclopropyl-3-(4-oxo-1H-pyrimidin-6-yl)propanoate
Reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[C:15]([O:17]C)[N:14]=[CH:13][N:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.[Cl-].[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C=O)C.C(#N)C>[CH:1]1([CH:4]([C:11]2[CH:16]=[C:15]([OH:17])[N:14]=[CH:13][N:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 130 °C
Procedure
Under a nitrogen atmosphere, to a solution of ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)propanoate (entire amount) in DMF (15 mL) was added pyridinium chloride (25.9 g), and the mixture was stirred at 130° C. for 20 min. The reaction mixture was cooled to 0° C. and diluted with acetonitrile (20 mL). Sodium hydrogen carbonate (17.0 g) was added to the reaction mixture, the insoluble material was filtered off, and the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was washed with diisopropyl ether to give the title compound (3.66 g) as a white solid.
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- filtrationthe insoluble material was filtered off
- customthe solvent in the filtrate was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
- washthe obtained solid was washed with diisopropyl ether
Sources & evidence
- ORD record
- ord-e6dc28229f74484fa35d70feccfd64c6
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181186B2
Reaction notes
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