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

HRID 1290803ノート

反応式

HRID 1290803 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒3 回

実験手順

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.)

後処理

  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

出典と根拠

ORDレコード
ord-abde492897ea4b179e34d925d5831423
出典データセット
uspto-grants-1998_05
特許番号
US05753665

反応ノート

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