Trifluoroacetic acid → HCID 66597624, 화합물

HRID 2276292노트

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HRID 2276292 반응식
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]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzeneHCID 49819035HCID 49819035, 화합물

생성물 1

HCID 66597624HCID 66597624, 화합물수율 71%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cdceeb49d898453a8e2c82956757952a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09132130B2

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