Water → HCID 57597200, compound

HRID 1787042Notes

Reaction equation

HRID 1787042 reaction equation
[Si]([O:8][CH2:9][C:10]#[C:11][CH2:12][N:13]1[C:21]2[C:20](Cl)=[N:19][CH:18]=[N:17][C:16]=2[CH:15]=[CH:14]1)(C(C)(C)C)(C)C.[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:41])([F:40])[F:39])[CH:33]=1)[NH2:27].O>C(O)(C)C>[Cl:23][C:24]1[CH:25]=[C:26]([NH:27][C:20]2[C:21]3[N:13]([CH2:12][C:11]#[C:10][CH2:9][OH:8])[CH:14]=[CH:15][C:16]=3[N:17]=[CH:18][N:19]=2)[CH:28]=[CH:29][C:30]=1[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([C:38]([F:40])([F:41])[F:39])[CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 196269843-Chloro-4-[3-(trifluoromethyl)phenoxy]anilineHCID 86615780HCID 86615780, compound

Product 1

HCID 57597200HCID 57597200, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

5-(4-{[Tert-butyl(dimethyl)silyl]oxy}but-2-yn-1-yl)-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (408.3 mg) was dissolved in isopropyl alcohol (7 mL), 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (421.0 mg) was added, and the mixture was stirred at 80° C. for 6 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained oil was dissolved in tetrahydrofuran (6 mL), a 1.0 M solution (2 mL) of tetrabutylammonium fluoride in tetrahydrofuran was added, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=67:33→20:80) and crystallized from hexane/ethyl acetate to give the title compound (425 mg) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe obtained oil was dissolved in tetrahydrofuran (6 mL)
  6. additiona 1.0 M solution (2 mL) of tetrabutylammonium fluoride in tetrahydrofuran was added
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. additionTo the reaction mixture was added saturated aqueous ammonium chloride solution
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was separated
  14. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=67:33→20:80)
  15. customcrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-bfd3ab9b54804d81a3cff037051f5e76
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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