Sodium ethoxide → 3-butyl-8-chloro-1-{4-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

HRID 1097698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097698
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=O)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4].O[NH:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)=[NH:29].[O-]CC.[Na+]>CCO>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[NH:10][C:9]=2[C:8](=[O:15])[N:7]([CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[O:22][N:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)[N:27]=2)[C:6]1=[O:25])[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 59395413ethyl 5-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoateHCID 178513306HCID 178513306, Verbindung

Produkt 1

HCID 593956363-butyl-8-chloro-1-{4-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]butyl}-3,7-dihydro-1H-purine-2,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a mixture of ethyl 5-(3-butyl-8-chloro-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (120 mg, 0.32 mmol) and of N-hydroxy-2-pyridinecarboximidamide (50 mg, 0.36 mmol) in EtOH (2 ml) was added a 21% (w/v) solution of sodium ethoxide in EtOH (0.225 ml, 0.62 mmol) and then heated in a sealed vial in a microwave oven at 140° C. for 10 min. The cooled mixture was evaporated to dryness and the residue partitioned between chloroform (5 ml) and saturated aqueous ammonium chloride (5 ml). The organic phase was evaporated to dryness and the crude product subjected to purification by MDAP. Product containing fractions were combined and evaporated to dryness. The product was triturated to a solid in a small amount of diethyl ether then dried to reveal the title compound as a white solid (44 mg, 31%).

Aufarbeitung

  1. customThe cooled mixture was evaporated to dryness
  2. customthe residue partitioned between chloroform (5 ml) and saturated aqueous ammonium chloride (5 ml)
  3. customThe organic phase was evaporated to dryness
  4. customthe crude product subjected to purification by MDAP
  5. additionProduct containing fractions
  6. customevaporated to dryness
  7. customThe product was triturated to a solid in a small amount of diethyl ether
  8. customthen dried

Quellen und Nachweise

ORD-Eintrag
ord-a5ce854c27e84d26885e53a2ff360a3c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

Notizen zur Reaktion

Wird geladen…