Hydrochloric Acid → 4-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]butan-1-ol

HRID 1926058Notes

Reaction equation

HRID 1926058 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:17]2[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=4)=[C:21]([Cl:36])[CH:20]=3)=[N:15][CH:14]=[N:13][C:12]=2[CH:11]=[CH:10]1)(=O)C.[OH-].[Na+].Cl.O>O1CCCC1>[Cl:36][C:21]1[CH:20]=[C:19]([NH:18][C:16]2[C:17]3[N:9]([CH2:8][CH2:7][CH2:6][CH2:5][OH:4])[CH:10]=[CH:11][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:24]=[CH:23][C:22]=1[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 675212554-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]butyl acetate

Product 1

HCID 575972694-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]butan-1-olYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]butyl acetate (281 mg) in tetrahydrofuran (4.0 mL) was added 1N aqueous sodium hydroxide solution (2.8 mL), and the mixture was stirred at room temperature for 4.5 hrs. 1N Aqueous hydrochloric acid solution (2.8 mL) was added, and the mixture was stirred for 15 min. The reaction mixture was poured into water (50 mL), and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was washed successively with 5% aqueous sodium hydrogen carbonate solution, water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to basic silica gel chromatography (eluent:hexane/ethyl acetate=95/5→0/100). The object fraction was concentrated under reduced pressure and dried. Ethanol/diisopropyl ether (5/95) was added to the residue, and the mixture was stirred with heating to 80° C., allowed to cool to room temperature, and stood still. The resultant precipitate was collected by filtration. The obtained precipitate was washed with diisopropyl ether and dried under reduced pressure to give the title compound (214 mg) as white powder crystals.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. extractionthe mixture was extracted with ethyl acetate (50 mL×3)
  3. washThe organic layer was washed successively with 5% aqueous sodium hydrogen carbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. customdried
  8. additionEthanol/diisopropyl ether (5/95) was added to the residue
  9. stirringthe mixture was stirred
  10. temperaturewith heating to 80° C.
  11. temperatureto cool to room temperature
  12. filtrationThe resultant precipitate was collected by filtration
  13. washThe obtained precipitate was washed with diisopropyl ether
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-1087bc3e41aa4ff4877ba4796223f6a3
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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