Acetic Anhydride → HCID 25062429, compound

HRID 1666226Notes

Reaction equation

HRID 1666226 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:18]([CH3:19])[C:17]3[C:16](=[O:20])[N:15]([CH2:21][C:22]#[CH:23])[C:14](=[O:24])[N:13]([CH3:25])[C:12]=3[N:11]=2)[CH:5]=[CH:6][CH:7]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C([O-])(O)=O.[Na+]>[C:26]([O:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:18]([CH3:19])[C:17]3[C:16](=[O:20])[N:15]([CH2:21][C:22]#[CH:23])[C:14](=[O:24])[N:13]([CH3:25])[C:12]=3[N:11]=2)[CH:5]=[CH:6][CH:7]=1)(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 25062427HCID 25062427, compound

Product 1

HCID 25062429HCID 25062429, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 0.1 mmol of 8-(3-hydroxyphenylethynyl)-3,7-dimethyl-1-prop-2-ynyl-3,7-dihydropurine-2,6-dione and 0.5 mL acetic anhydride was heated under reflux for 15 min. Subsequently the mixture was hydrolyzed with concentrated NaHCO3-solution (50 mL) and the product was extracted with dichloromethane. The organic extracts were dried over MgSO4 and filtered and concentrated under vacuum. The crystalline residue was treated with ether and filtered under reduced pressure yielding 8-(3-acetoxyphenylethynyl)-3,7-dimethyl-1-prop-2-ynyl-3,7-dihydropurine-2,6-dione: colorless crystals (yield >95%), m.p. 238° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 min
  3. extractionthe product was extracted with dichloromethane
  4. dry with materialThe organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. additionThe crystalline residue was treated with ether
  8. filtrationfiltered under reduced pressure

Sources & evidence

ORD record
ord-dececcde78984d5a902d9aa958672f2d
Source dataset
uspto-grants-2011_10
Patent number
US08044061B2

Reaction notes

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