Hydrochloric Acid → HCID 59309785, compound

HRID 1513065Notes

Reaction equation

HRID 1513065 reaction equation
C([O:5][C:6]([C:8]1[N:16]=[CH:15][N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:38])[N:12]2[C:17]1[CH:22]=[C:21]([O:23][CH2:24][C:25]2[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[C:27]([F:33])[C:26]=2[F:34])[C:20]([O:35][CH3:36])=[CH:19][C:18]=1[Cl:37])=O)CCC.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:37][C:18]1[CH:19]=[C:20]([O:35][CH3:36])[C:21]([O:23][CH2:24][C:25]2[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[C:27]([F:33])[C:26]=2[F:34])=[CH:22][C:17]=1[N:12]1[C:11](=[O:38])[NH:10][C:9]2[C:13]1=[N:14][CH:15]=[N:16][C:8]=2[CH2:6][OH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 59310144HCID 59310144, compound

Product 1

HCID 59309785HCID 59309785, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(n-butoxycarbonyl)-9-[2-chloro-5-(2,3-difluoro-6-methoxy-benzyloxy)-4-methoxyphenyl]-7,9-dihydro-8H-purin-8-one (0.82 g) in tetrahydrofuran (25 mL) was added diisobutylaluminium hydride (0.93 mol/L n-hexane solution, 4.03 mL) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes, and then stirred at room temperature for 3 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate) to give the title compound (0.6 g).

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature for 3 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-ac83f08ad2384d7db8e4d49a13cfbb4a
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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