Reaction equation
[Mg].Br[CH:3](C)C.C([Mg]Br)(C)C.[CH3:11][O:12][C:13]1[C:18]([CH:19]=O)=[C:17]([O:21][CH3:22])[N:16]=[CH:15][N:14]=1.[Cl-].[NH4+].[O:25]1[CH2:29][CH2:28][CH2:27]C1>>[CH3:11][O:12][C:13]1[C:18]([CH2:19][CH:29]([OH:25])[CH:28]([CH3:3])[CH3:27])=[C:17]([O:21][CH3:22])[N:16]=[CH:15][N:14]=1Participants
Procedure
0.81 g (33 mmol) of magnesium was added to 30 ml of tetrahydrofuran, and 4.1 g (33 mmol) of 2-bromopropane was added to prepare a tetrahydrofuran solution of isopropyl magnesium bromide. 2.8 g (17 mmol) of 4,6-dimethoxypyrimidine-5-carboaldehyde was dissolved in 50 ml of tetrahydrofuran, and the solution was added to the above tetrahydrofuran solution at room temperature and reacted overnight. The reaction solution was poured into an aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with an aqueous citric acid solution, water and an aqueous sodium chloride solution in this order, dried and concentrated, and the obtained oily product was purified by column chromatography (ethyl acetate:n-hexane=1:4) to obtain 1.9 g (yield: 54%) of 1-(4,6-dimethoxy pyrimidin-5-yl)-3-methylbutan-2-ol as slightly yellow crystals.
Workup
- additionwas added
- customreacted overnight
- extractionextracted with ethyl acetate
- washThe organic layer was washed with an aqueous citric acid solution, water
- dry with materialan aqueous sodium chloride solution in this order, dried
- concentrationconcentrated
- customthe obtained oily product was purified by column chromatography (ethyl acetate:n-hexane=1:4)
Sources & evidence
- ORD record
- ord-d022aedc6a5e46c7be25577186f30d77
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06806230B1
Linked notes
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