Trifluoroacetic acid → HCID 66597624, compound

HRID 2276292Notes

Reaction equation

HRID 2276292 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 66597624HCID 66597624, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cdceeb49d898453a8e2c82956757952a
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Reaction notes

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