Trifluoroacetic acid → HCID 66597624、化合物

HRID 2276292ノート

反応式

HRID 2276292 の反応式
FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[CH2:16]([C:18]1[N:19]([CH3:43])[C:20]2[C:25]([N:26]=1)=[C:24]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[N:23]=[C:22]([S:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[N:21]=2)[CH3:17].[N+:44](C1C=C(C=CC=1OC)CBr)([O-:46])=[O:45]>CC(C)=O>[CH2:16]([C:18]1[N:19]([CH3:43])[C:20]2[C:25]([N:26]=1)=[C:24]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[N:23]=[C:22]([S:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([N+:44]([O-:46])=[O:45])[CH:36]=1)[N:21]=2)[CH3:17]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzeneHCID 49819035HCID 49819035、化合物

生成物 1

HCID 66597624HCID 66597624、化合物収率 71%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
80 °C

実験手順

Trifluoroacetic acid (40 ml) and anisole (2.7 ml, 15 mmol) were added to 8-ethyl-2-(4-methoxybenzylsulfanyl)-9-methyl-6-morpholino-9H-purine (5.0 g, 12.5 mmol), and heated and stirred at 80° C. overnight. After distilling away trifluoroacetic acid under reduced pressure, neutralization was performed by adding excess triethylamine under ice cooling. After distilling away triethylamine under reduced pressure, the residue was dissolved in acetone (50 ml) and 3-nitro-4-methoxybenzyl bromide (3.69 g, 15 mmol) dissolved in acetone (10 ml) was added. After stirring at room temperature for 2.5 hours, the reaction solution was concentrated under reduced pressure, the residue was made to have a pH of approximately 7.0 by 2N—NaOH solution, and the precipitated crystals were collected by filtration. The obtained crystals were washed sequentially with hexane and ether to obtain 3.93 g (71% yield) of 8-ethyl-9-methyl-6-morpholino-2-(3-nitro-4-methoxybenzylsulfanyl)-9H-purine.

後処理

  1. temperatureheated
  2. distillationAfter distilling away trifluoroacetic acid under reduced pressure, neutralization
  3. additionby adding excess triethylamine under ice cooling
  4. distillationAfter distilling away triethylamine under reduced pressure
  5. dissolutionthe residue was dissolved in acetone (50 ml)
  6. additionwas added
  7. stirringAfter stirring at room temperature for 2.5 hours
  8. concentrationthe reaction solution was concentrated under reduced pressure
  9. filtrationthe precipitated crystals were collected by filtration
  10. washThe obtained crystals were washed sequentially with hexane and ether

出典と根拠

ORDレコード
ord-cdceeb49d898453a8e2c82956757952a
出典データセット
uspto-grants-2015_09
特許番号
US09132130B2

反応ノート

読み込み中…