2-Hydrazinoadenosine → Ethyl 1-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

HRID 39121

Reaktionsgleichung

Reaktionsgleichung von HRID 39121
[CH:1]([CH:3]([CH:9]=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=O.[NH:11]([C:13]1[N:14]=[C:15]([NH2:31])[C:16]2[N:17]=[CH:18][N:19]([C:29]=2[N:30]=1)[C@@H:20]1[O:28][C@H:25]([CH2:26][OH:27])[C@@H:23]([OH:24])[C@H:21]1[OH:22])[NH2:12]>CC(O)C>[OH:22][C@@H:21]1[C@H:23]([OH:24])[C@@H:25]([CH2:26][OH:27])[O:28][C@H:20]1[N:19]1[CH:18]=[N:17][C:16]2[C:29]1=[N:30][C:13]([N:11]1[CH:1]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:9]=[N:12]1)=[N:14][C:15]=2[NH2:31]

Komponenten

4

Edukt 2

HCID 103572622-HydrazinoadenosineHCID 11029955Ethyl 2-formyl-3-oxopropanoate

Produkt 1

HCID 9865974Ethyl 1-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Ethyl 2-formyl-3-oxopropionate (23.93 g, 0.17 mol) was placed in a flask equipped with mechanical stirrer, gas inlet, gas outlet and reflux condenser. 2-Propanol was added to the flask followed by 2-hydrazinoadenosine (44.45 g, 0.15 mol). The mixture was heated to reflux under stirring for 2-4 hours, following the progress of the reaction by TLC analysis. When the reaction was judged complete, the heat source was removed and the mixture cooled to room temperature. The suspension was cooled under stirring in an ice-bath for 1.5 to 2 hours. The solids were isolated by vacuum filtration, and washed with ice-cold 2-propanol. The product, ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate, was dried under reduced pressure to a constant weight. Yield 54.29 g, purity (by HPLC) 96.6%.

Aufarbeitung

  1. customequipped with mechanical stirrer, gas inlet, gas outlet
  2. temperaturereflux condenser
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. customthe progress of the reaction by TLC analysis
  6. customthe heat source was removed
  7. temperatureThe suspension was cooled
  8. stirringunder stirring in an ice-bath for 1.5 to 2 hours
  9. customThe solids were isolated by vacuum filtration
  10. washwashed with ice-cold 2-propanol
  11. dry with materialThe product, ethyl 1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxylate, was dried under reduced pressure to a constant weight

Quellen und Nachweise

ORD-Eintrag
ord-241334186ae143709ad5992f30788498
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524883B2

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