Hydrochloric Acid → HCID 59309626, compound

HRID 1513061Notes

Reaction equation

HRID 1513061 reaction equation
[Cl:1][C:2]1[C:7](OC)=[C:6]([O:10]C)[C:5]([O:12][CH2:13][C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]([F:22])[C:15]=2[F:23])=[CH:4][C:3]=1[N:24]1[C:32](=[O:33])[NH:31][C:30]2[C:25]1=[N:26][C:27]([CH3:36])=[N:28][C:29]=2[O:34][CH3:35].CO.Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([OH:10])[C:5]([O:12][CH2:13][C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[C:16]([F:22])[C:15]=2[F:23])=[CH:4][C:3]=1[N:24]1[C:32](=[O:33])[NH:31][C:30]2[C:25]1=[N:26][C:27]([CH3:36])=[N:28][C:29]=2[O:34][CH3:35]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86641284HCID 86641284, compound

Product 1

HCID 59309626HCID 59309626, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxy-methyloxyphenyl]-6-methoxy-2-methyl-7,9-dihydro-8H-purin-8-one (80 mg) in tetrahydrofuran (2 mL)-methanol (1 mL) was added concentrated hydrochloric acid (0.1 mL), and the mixture was stirred at room temperature for 2 hours, and then stirred at 60° C. for 1 hour. The reaction mixture was diluted with water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with 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: n-hexane/ethyl acetate=1/1−1/3) to give the title compound (22 mg).

Workup

  1. stirringstirred at 60° C. for 1 hour
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1−1/3)

Sources & evidence

ORD record
ord-9f500da3c1434aa88cf8390018cd9156
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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