Methanol → 4-Methoxy-6-(1H-pyrazol-1-yl)pyrimidine
Reaction equation
[Na].Cl[C:3]1[N:8]=[CH:7][N:6]=[C:5]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)[CH:4]=1.[CH3:14][OH:15]>>[CH3:14][O:15][C:3]1[N:8]=[CH:7][N:6]=[C:5]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)[CH:4]=1Participants
Procedure
In 3 ml of anhydrous methanol, 23 mg of sodium metal was dissolved, and to the resulting solution, 180 mg of 6-chloro-4-(1-pyrazolyl)pyrimidine in 2 ml of anhydrous methanol was added dropwise with stirring at room temperature in a stream of nitrogen overnight. The solvent was distilled off under reduced pressure, and the residue was extracted with 20 ml of methylene chloride. The organic layer was washed with 5 ml of saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled away, and a residue was purified by a silica gel column chromatography using chloroform to give an amorphous product. The product was recrystallized from n-hexane to provide 132 mg of the plate crystal 6-methoxy-4-(1-pyrazolyl)pyrimidine having a melting point of 108.5°-109° C.
Workup
- distillationThe solvent was distilled off under reduced pressure
- extractionthe residue was extracted with 20 ml of methylene chloride
- washThe organic layer was washed with 5 ml of saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled away
- customa residue was purified by a silica gel column chromatography
- customto give an amorphous product
- customThe product was recrystallized from n-hexane
Sources & evidence
- ORD record
- ord-26a0830f0a944518a69cdfa0cae8def5
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04849424
Reaction notes
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