Tetrahydrofuran → 2-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)acetaldehyde

HRID 1452615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452615
C1C[O:4]CC1.[CH2:6]([C:9]1[C:10]([Cl:19])=[N:11][C:12]2[N:13]([N:16]=[CH:17][CH:18]=2)[C:14]=1[Cl:15])[CH:7]=C.I([O-])(=O)(=O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.O>[Cl:19][C:10]1[C:9]([CH2:6][CH:7]=[O:4])=[C:14]([Cl:15])[N:13]2[N:16]=[CH:17][CH:18]=[C:12]2[N:11]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 24437Sodium SulfiteHCID 23667635Sodium periodateHCID 575268456-Allyl-5,7-dichloropyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 866137832-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixed solution of THF (24 mL) and water (6 mL) containing 6-allyl-5,7-dichloropyrazolo[1,5-a]pyrimidine (1.82 g, 7.89 mmol), sodium periodate (5.12 g, 23.9 mmol) and osmium tetraoxide (2.5w/v % in tert-butanol, 3 mL, 0.23 mmol) were added with ice-cooling. After this mixture was stirred at room temperature for 3 hr, aqueous sodium sulfite was added here. The resultant mixture was extracted with ethyl acetate and the organic layer was washed with aqueous sodium hydrogen carbonate and then brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off to obtain 5,7-dichloro-6-(2-oxoethyl)pyrazolo[1,5-a]pyrimidine.

Aufarbeitung

  1. additionwere added with ice-
  2. temperaturecooling
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with aqueous sodium hydrogen carbonate
  5. dry with materialbrine and dried over sodium sulfate
  6. filtrationAfter the sodium sulfate was filtered off
  7. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-4593c2454b6148dcb859fd46d5e0cbac
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473694B2

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