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

HRID 1097670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097670
[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.[OH:27][NH:28]/[C:29](=[N:38]\[H])/[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=1.[O-]CC.[Na+]>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:27][N:28]=[C:29]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=4)[N:38]=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 178506465N'-hydroxy-2-(4-hydroxyphenyl)ethanimidamide

Produkt 1

HCID 593957908-Chloro-1-(3-{3-[(4-hydroxyphenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dioneAusbeute 17,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (29 mg, 0.078 mmol) and (1Z)—N-hydroxy-2-(4-hydroxyphenyl)ethanimidamide (14 mg, 0.084 mmol) were heated in EtOH (1 ml) with 21% ethanolic sodium ethoxide (0.043 ml, 0.117 mmol) under microwave irradiation at 140° C. for 10 min. The mixture was partitioned between EtOAc and 2M HCl and the organic phase evaporated. This material was stirred with EtOH (1 ml) and 2M NaOH (0.5 ml) for 18 h, before being worked up again by partition between EtOAc and 2M HCl. Purification by MDAP afforded the title compound (6.5 mg).

Aufarbeitung

  1. customThe mixture was partitioned between EtOAc and 2M HCl
  2. customthe organic phase evaporated
  3. customby partition between EtOAc and 2M HCl
  4. customPurification by MDAP

Quellen und Nachweise

ORD-Eintrag
ord-bc191e1f4aa443b5931a004c1a990bd2
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

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