Sulfuric Acid → 5-(5-Acetyl-2-butoxy-3-pridinyl)-2-[2-(dimethylamino)ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 354191

Reaktionsgleichung

Reaktionsgleichung von HRID 354191
S(=O)(=O)(O)[OH:2].[CH2:6]([O:10][C:11]1[C:16]([C:17]2[NH:18][C:19](=[O:33])[C:20]3[C:21](=[C:23]([CH2:31][CH3:32])[N:24]([CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])[N:25]=3)[N:22]=2)=[CH:15][C:14]([C:34]#[CH:35])=[CH:13][N:12]=1)[CH2:7][CH2:8][CH3:9]>CC(C)=O.CO.S([O-])([O-])(=O)=O.[Hg+2]>[C:34]([C:14]1[CH:15]=[C:16]([C:17]2[NH:18][C:19](=[O:33])[C:20]3[C:21](=[C:23]([CH2:31][CH3:32])[N:24]([CH2:26][CH2:27][N:28]([CH3:29])[CH3:30])[N:25]=3)[N:22]=2)[C:11]([O:10][CH2:6][CH2:7][CH2:8][CH3:9])=[N:12][CH:13]=1)(=[O:2])[CH3:35]

Komponenten

6

Edukt 2

HCID 1118Sulfuric AcidHCID 1356742315-(2-Butoxy-5-ethynyl-3-pyridinyl)-2-[2-(dimethylamino)ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Produkt 1

HCID 1354447225-(5-Acetyl-2-butoxy-3-pridinyl)-2-[2-(dimethylamino)ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24544Mercuric sulfateKatalysatorHCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

1 N Sulfuric acid (1 mL) was added to a stirred solution of 5-(2-butoxy-5-ethynyl-3-pyridinyl)-2-[2-(dimethylamino)ethyl]-3-ethyl-2,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Example 46) (280 mg, 0.69 mmol) in acetone (8 mL) at room temperature. Mercury sulfate (40 mg, 0.14 mmol) was added and the mixture heated at reflux for 5 h. The reaction mixture was cooled, diluted with methanol (10 mL), filtered and the filtrate washed with further methanol. The solvent was evaporated and the residue partitioned between ethyl acetate (100 mL) and saturated sodium bicarbonate solution (100 mL). The aqueous was washed with a further 100 mL of ethyl acetate and the combined organics dried (MgSO4) and concentrated. Purification by flash column chromatography (elution with 95% dichloromethane/methanol) gave the product as a cream coloured solid (140 mg).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 5 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. washthe filtrate washed with further methanol
  6. customThe solvent was evaporated
  7. customthe residue partitioned between ethyl acetate (100 mL) and saturated sodium bicarbonate solution (100 mL)
  8. washThe aqueous was washed with a further 100 mL of ethyl acetate
  9. dry with materialthe combined organics dried (MgSO4)
  10. concentrationconcentrated
  11. customPurification
  12. washby flash column chromatography (elution with 95% dichloromethane/methanol)
  13. customgave the product as a cream

Quellen und Nachweise

ORD-Eintrag
ord-4a0161489eee48d1a7fb50cdbbb050c3
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756373B1

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