Sodium hydride → 7-[1-(4-Trifluoromethylphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine

HRID 1290800ノート

反応式

HRID 1290800 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH:15]([C:17]1[N:22]2[N:23]=[CH:24][N:25]=[C:21]2[N:20]=[CH:19][CH:18]=1)[CH3:16]>COCCOC>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([O:9][CH:15]([C:17]2[N:22]3[N:23]=[CH:24][N:25]=[C:21]3[N:20]=[CH:19][CH:18]=2)[CH3:16])=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 678744-(Trifluoromethyl)phenolHCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

生成物 1

HCID 98395757-[1-(4-Trifluoromethylphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

4-Trifluoromethylphenol (1.62 g) was added to a stirred suspension of sodium hydride (0.48 g) in dry 1,2-dimethoxyethane (35 ml). The mixture was stirred at room temperature for 30 minutes, then a solution of 7-(1-bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine (2.27 g, prepared in a similar manner to that described in Example 6 below) in dry 1,2-dimethoxyethane (85 ml) was added dropwise. The mixture was stirred at room temperature for 24 hours. The sodium bromide was removed from the mixture by filtration. The solvent was evaporated from the filtrate and the residue dissolved in dichloromethane and washed with 200 ml of a 5% aqueous solution of sodium hydroxide followed by water. The organic layer was dried over magnesium sulphate. Evaporation of the solvent afforded a crude product which was purified by column chromatography on silica gel using as eluent a mixture of petroleum ether and ethyl acetate (in the ratio 6:4 respectively), followed by recrystallisation from hexane, to give 7-[1-(4-trifluoromethylphenoxy)ethyl]-1,2,4-triazolo[1,5-a]pyrimidine. Yield 1.1 g, (mp 100°-102° C.).

後処理

  1. additionwas added dropwise
  2. stirringThe mixture was stirred at room temperature for 24 hours
  3. customThe sodium bromide was removed from the mixture by filtration
  4. customThe solvent was evaporated from the filtrate
  5. dissolutionthe residue dissolved in dichloromethane
  6. washwashed with 200 ml of a 5% aqueous solution of sodium hydroxide
  7. dry with materialThe organic layer was dried over magnesium sulphate
  8. customEvaporation of the solvent
  9. customafforded a crude product which
  10. customwas purified by column chromatography on silica gel using as eluent
  11. additiona mixture of petroleum ether and ethyl acetate (in the ratio 6:4 respectively),
  12. customfollowed by recrystallisation from hexane

出典と根拠

ORDレコード
ord-04009d33501e4c57ab782c08e16704d7
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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