Hydrochloric Acid → Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoate
Reaction equation
C(O)C.[H-].[Na+].[N:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14]CC)=O)=[N:8][CH:7]=1.[C:17]([O:20][CH2:21][CH3:22])(=[O:19])[CH3:18].Cl.C(=O)(O)[O-].[Na+]>C(OCC)C.C1(C)C=CC=CC=1>[O:14]=[C:12]([C:9]1[CH:10]=[CH:11][N:6]=[CH:7][N:8]=1)[CH2:18][C:17]([O:20][CH2:21][CH3:22])=[O:19]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A solution of ethanol (16.18 g, 0.351 mol) in diethyl ether (15 ml) was added to a solution of sodium hydride (13.71 g, 0.343 mol, 60% in paraffin, paraffin was removed by washing with hexane) in diethyl ether (100 ml). After stirring the mixture for 30 minutes, the solvent was evaporated under reduced pressure, and toluene (100 ml) was added to the residue. The solution was added with a solution of ethyl pyrimidine-4-carboxylate (intermediate 5, 30.86 g, 0.203 mol) and ethyl acetate (30.48 g, 0.346 mol) in toluene (100 ml), and the mixture was heated at 80° C. for 3 hours. The mixture was added with hydrochloric acid and then sodium bicarbonate to be adjusted to pH 4. The solution was partitioned between water and ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give ethyl 3-oxo-3-(pyrimidin-4-yl)propionate (intermediate 6, 36.10 g, 92%).
Workup
- customthe solvent was evaporated under reduced pressure, and toluene (100 ml)
- additionwas added to the residue
- customThe solution was partitioned between water and ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-4e64f84356544c568c2593fc7e818f42
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288383B2
Reaction notes
Loading…