Hydrochloric Acid → HCID 59309902, compound

HRID 1513063Notes

Reaction equation

HRID 1513063 reaction equation
C([O:4][CH2:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][C:11](=[O:40])[N:12]2[C:15]2[CH:20]=[C:19]([O:21][CH2:22][C:23]3[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=3[F:31])[C:18]([O:32][CH2:33][C:34](OCC)=[O:35])=[CH:17][C:16]=2[Cl:39])=[C:8]([O:41][CH3:42])[N:7]=1)(=O)C.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[Cl:39][C:16]1[CH:17]=[C:18]([O:32][CH2:33][CH2:34][OH:35])[C:19]([O:21][CH2:22][C:23]2[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[F:31])=[CH:20][C:15]=1[N:12]1[C:11](=[O:40])[NH:10][C:9]2[C:13]1=[N:14][C:6]([CH2:5][OH:4])=[N:7][C:8]=2[O:41][CH3:42]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 59309828HCID 59309828, compound

Product 1

HCID 59309902HCID 59309902, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-acetyloxymethyl-9-[2-chloro-4-ethoxycarbonylmethoxy-5-(2-fluoro-6-methoxybenzyloxy)phenyl]-6-methoxy-7,9-dihydro-8H-purin-8-one (0.1 g) in tetrahydrofuran (3.3 mL) was added diisobutylaluminium hydride (0.99 mol/L toluene solution, 1 mL) under ice-cooling, and the mixture was stirred at the same temperature for 2 hours, and then stirred at room temperature for 1 hour. 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 brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate−ethyl acetate/methanol=6/1) to give the title compound (30 mg).

Workup

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

Sources & evidence

ORD record
ord-747e2b30c47641308f86f9bf3c978c03
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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