Water → HCID 59310100, compound

HRID 1513068Notes

Reaction equation

HRID 1513068 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[CH:4][C:3]=1[N:22]1[C:30](=[O:31])[NH:29][C:28]2[C:23]1=[N:24][C:25]([CH2:34][OH:35])=[N:26][C:27]=2[O:32][CH3:33].CC([OH:39])C.O.C(OCC)(=O)C>CC(C)=O>[C:34]([C:25]1[N:24]=[C:23]2[C:28]([NH:29][C:30](=[O:31])[N:22]2[C:3]2[CH:4]=[C:5]([O:10][CH2:11][C:12]3[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=3[F:21])[C:6]([O:8][CH3:9])=[CH:7][C:2]=2[Cl:1])=[C:27]([O:32][CH3:33])[N:26]=1)([OH:39])=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 59309735HCID 59309735, compound

Product 1

HCID 59310100HCID 59310100, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-2-hydroxymethyl-6-methoxy-7,9-dihydro-8H-purin-8-one (0.14 g) in acetone (5 mL) was added this solution in a dropwise manner under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes, and then stirred at room temperature overnight. To the reaction mixture was added 2-propanol (2 mL), and the mixture was stirred at room temperature for 20 minutes. To the mixture were added water and ethyl acetate, and the insoluble material was removed by filtration. The insoluble material was washed with water, ethyl acetate and diethyl ether successively. The filtrate and washings were combined, and the organic layer was separated. The organic layer 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−ethyl acetate/methanol=1/1) to give the title compound (4 mg).

Workup

  1. temperaturecooling
  2. stirringstirred at room temperature overnight
  3. stirringthe mixture was stirred at room temperature for 20 minutes
  4. customthe insoluble material was removed by filtration
  5. washThe insoluble material was washed with water, ethyl acetate and diethyl ether successively
  6. customthe organic layer was separated
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate−ethyl acetate/methanol=1/1)

Sources & evidence

ORD record
ord-27e6f93e179441d3a0cef6f170b8562f
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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