Diethyl Ether → 4-Benzyl-2,6-dichloropyrimidine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH2:10]([Mg]Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OCC)C>O1CCCC1>[CH2:10]([C:6]1[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([Cl:9])[CH:5]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
To a solution of 2,4,6-trichloropyrimidine (936 mg, 5.0 mmol) in tetrahydrofuran (50 mL) was added at −78° C. under an atmosphere of nitrogen and stirring drop wise 1 M benzylmagnesium chloride solution in diethyl ether (5 mL, 5.0 mmol). The reaction was let to warm up to 20° C. over 16 h. The solvent was removed under reduced pressure and the residue was dissolved in water. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed once with brine, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using heptane and then heptane/ethyl acetate (9:1 v/v) as eluent to yield the title compound (778 mg, 65%) as a pale-yellow viscous oil.
Workup
- customThe solvent was removed under reduced pressure
- dissolutionthe residue was dissolved in water
- extractionThe aqueous layer was extracted twice with dichloromethane
- washThe combined organic layers were washed once with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-ad596dc81cb3406a86fc463e7152bdfe
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962834B2
Reaction notes
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