Sodium Azide → 9-Allyl-6-pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-one

HRID 600580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600580
[CH2:1]([N:4]1[C:12]2[C:11](Cl)=[N:10][C:9](=[O:14])[N:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].[N-:20]=[N+:21]=[N-:22].[Na+]>C(O)C>[CH2:1]([N:4]1[C:12]2[C:11]3=[N:20][N:21]=[N:22][N:10]3[C:9](=[O:14])[N:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 598538197-Allyl-6-chloro-3-pentyl-3,7-dihydro-2H-purin-2-one

Produkt 1

HCID 598538529-Allyl-6-pentyl-6,9-dihydro-5H-tetrazolo[5,1-i]purin-5-oneAusbeute 22,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 7-allyl-6-chloro-3-pentyl-3,7-dihydro-2H-purin-2-one (0.65 g, 2.3 mmol) and sodium azide (0.98 g, 15 mmol) in ethanol (20 mL) was refluxed overnight. The reaction mixture was concentrated under vacuum. The residue was diluted with water and EtOAc. The organic phase was separated and the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by preparative LCMS to provide the desired product as a white powder (0.15 g, 22.6%). LCMS calculated for C13H18N7O (M+H): 288.2. found: 288.1.

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. additionThe residue was diluted with water and EtOAc
  4. customThe organic phase was separated
  5. extractionthe aqueous layer was extracted with EtOAc twice
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customwas purified by preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-ad7c2f61b2ee4bb38521630e8b5090b9
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902205B2

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