4-Methoxyphenol → 7-[1-(4-Methoxyphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine

HRID 1290803노트

반응식

HRID 1290803 반응식
[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]=1

참가 물질

5

반응물 3

HCID 90154-MethoxyphenolHCID 24758Sodium hydrideHCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

생성물 1

HCID 98602317-[1-(4-Methoxyphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매3회

실험 절차

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.)

후처리

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. filtrationfiltered
  3. customthe solvent was evaporated from the filtrate under reduced pressure
  4. customThe residue was purified by flash chromatography
  5. additiona mixture of ethyl acetate and petroleum ether
  6. customfollowed by recrystallisation from a mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-abde492897ea4b179e34d925d5831423
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753665

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