Phosphorus oxychloride → 4-Chloro-6-(1,1-dimethylethyl)pyrimidine
Reaction equation
[C:1]([C:5]1[CH:10]=[C:9](O)[N:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:14])=O>>[C:1]([C:5]1[CH:10]=[C:9]([Cl:14])[N:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
Next, 4.7 g of 4-tert-butyl-6-hydroxypyrimidine obtained in Step 1 and 14 mL of phosphoryl chloride were put into a 50 mL three-neck flask, and the mixture was heated and refluxed for 1.5 hours. After the reflux, phosphoryl chloride was distilled off under reduced pressure. The obtained residue was dissolved in dichloromethane, washed with water and a saturated aqueous solution of sodium hydrogen carbonate, and dried with magnesium sulfate. After the drying, the solution was filtered. The solvent of this solution was distilled off, and then the obtained residue was purified by silica gel column chromatography using hexane and ethyl acetate as a developing solvent in a ratio of 10:1, so that the pyrimidine derivative to be produced was obtained as a white solid in a yield of 78%. A synthesis scheme of Step 2 is shown in (k-2).
Workup
- temperaturethe mixture was heated
- temperaturerefluxed for 1.5 hours
- distillationAfter the reflux, phosphoryl chloride was distilled off under reduced pressure
- dissolutionThe obtained residue was dissolved in dichloromethane
- washwashed with water
- dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and dried with magnesium sulfate
- filtrationAfter the drying, the solution was filtered
- distillationThe solvent of this solution was distilled off
- customthe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-fd0ae030b20444cc8b40cad5ac5ccf5b
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09127032B2
Reaction notes
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