4-Methoxyphenol → 7-[1-(4-Methoxyphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH:13]([C:15]1[N:20]2[N:21]=[CH:22][N:23]=[C:19]2[N:18]=[CH:17][CH:16]=1)[CH3:14]>COCCOC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH:13]([C:15]2[N:20]3[N:21]=[CH:22][N:23]=[C:19]3[N:18]=[CH:17][CH:16]=2)[CH3:14])=[CH:5][CH:4]=1Participants
Procedure
A solution of 4-methoxyphenol (1,24 g) in dry 1,2-dimethoxyethane was added slowly to a stirred suspension of sodium hydride (0.48 g) in dry 1,2-dimethoxyethane (35 ml). The mixture was stirred for 30 minutes, then a solution of 7-(1-bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine (2.27 g) in dry 1,2-dimethoxyethane (85 ml) was added dropwise. The reaction mixture was stirred overnight at room temperature, filtered and the solvent was evaporated from the filtrate under reduced pressure. The residue was purified by flash chromatography using as eluent a mixture of ethyl acetate and petroleum ether, followed by recrystallisation from a mixture of ethyl acetate and hexane, to give 7-[1-(4-methoxyphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 1.67 g (mp 112°-114° C.)
Workup
- stirringThe reaction mixture was stirred overnight at room temperature
- filtrationfiltered
- customthe solvent was evaporated from the filtrate under reduced pressure
- customThe residue was purified by flash chromatography
- additiona mixture of ethyl acetate and petroleum ether
- customfollowed by recrystallisation from a mixture of ethyl acetate and hexane
Sources & evidence
- ORD record
- ord-abde492897ea4b179e34d925d5831423
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05753665
Reaction notes
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