Acetic Anhydride → HCID 59309725, compound

HRID 1513087Notes

Reaction equation

HRID 1513087 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7](=[O:32])[N:8]2[C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]3[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[C:21]([F:27])[C:20]=3[F:28])[C:14]([O:29][CH3:30])=[CH:13][C:12]=2[Cl:31])=[C:4]([O:33][CH3:34])[N:3]=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>>[C:35]([NH:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][C:7](=[O:32])[N:8]2[C:11]2[CH:16]=[C:15]([O:17][CH2:18][C:19]3[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[C:21]([F:27])[C:20]=3[F:28])[C:14]([O:29][CH3:30])=[CH:13][C:12]=2[Cl:31])=[C:4]([O:33][CH3:34])[N:3]=1)(=[O:37])[CH3:36]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 59310119HCID 59310119, compound

Product 1

HCID 59309725HCID 59309725, compound

Conditions

Temperature
110 °C

Procedure

A mixture of 2-amino-9-[2-chloro-5-(2,3-difluoro-6-methoxybenzyloxy)-4-methoxyphenyl]-6-methoxy-7,9-dihydro-8H-purin-8-one (29 mg) and acetic anhydride (3 mL) was stirred at 110° C. in a reaction vessel equipped with a reflux condenser for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (2 mL). To the solution were added sodium methoxide (28% methanol solution, 2 mL) and water (1 mL), and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was poured into 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, and the solvent was removed under reduced pressure. To the residue was added a mixed solvent (n-hexane/ethyl acetate=1/1), and the precipitated crystals were collected by filtration. The collected crystals were washed with diethyl ether, and dried under reduced pressure to give the title compound (20 mg).

Workup

  1. customequipped with a reflux condenser for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in methanol (2 mL)
  4. additionTo the solution were added sodium methoxide (28% methanol solution, 2 mL) and water (1 mL)
  5. stirringthe mixture was stirred at room temperature for 15 minutes
  6. additionThe reaction mixture was poured into 1 mol/L hydrochloric acid
  7. extractionthe resulting mixture was extracted with ethyl acetate
  8. washThe extract was washed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was removed under reduced pressure
  11. additionTo the residue was added a mixed solvent (n-hexane/ethyl acetate=1/1)
  12. filtrationthe precipitated crystals were collected by filtration
  13. washThe collected crystals were washed with diethyl ether
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-a7c1db9892c74b819054f648162a095d
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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