Sodium ethoxide → 8-Chloro-1-(3-{3-[(3-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1097665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097665
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15]C(OCC)=O)[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1.CC[O-].[Na+].[Cl:31][C:32]1[CH:33]=[C:34]([CH2:38]/[C:39](=[N:42]/[H])/[NH:40][OH:41])[CH:35]=[CH:36][CH:37]=1>CCO>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][C:15]3[O:41][N:40]=[C:39]([CH2:38][C:34]4[CH:35]=[CH:36][CH:37]=[C:32]([Cl:31])[CH:33]=4)[N:42]=3)[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 66812467Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoateHCID 1785064602-(3-chlorophenyl)-N'-hydroxyethanimidamide

Produkt 1

HCID 593957758-Chloro-1-(3-{3-[(3-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dioneAusbeute 49,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (70 mg, 0.19 mmol) was dissolved in EtOH. The solution was treated with a 21% solution of NaOEt in EtOH (78 μl, 0.21 mmol) and (1Z)-2-(3-chlorophenyl)-N-hydroxyethanimidamide (38 mg, 0.21 mmol). The reaction was heated in the microwave at 140° C. for 10 min. The mixture was partitioned between EtOH and 2M HCl (aq). The organic layer was decanted off and concentrated. The crude product was purified on the MDAP. The product fractions were combined and concentrated to give the title compound as a white solid (46 mg, 49%).

Aufarbeitung

  1. customThe mixture was partitioned between EtOH and 2M HCl (aq)
  2. customThe organic layer was decanted off
  3. concentrationconcentrated
  4. customThe crude product was purified on the MDAP
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-821438c68be944fb954e5c87a25d879e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

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