Sodium Methoxide → diethyl 4-((6-amino-8-methoxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzylphosphonate

HRID 629932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629932
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:16][C:17]1[CH:31]=[CH:30][C:20]([CH2:21][P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[CH:19][CH:18]=1.[CH3:33][O-:34].[Na+]>CO>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:34][CH3:33])[N:6]2[CH2:16][C:17]1[CH:31]=[CH:30][C:20]([CH2:21][P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25])=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 86667760diethyl 4-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzylphosphonate

Produkt 1

HCID 86667759diethyl 4-((6-amino-8-methoxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzylphosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of diethyl 4-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzylphosphonate in methanol (0.10 M) was added sodium methoxide (20 equiv.). The reaction mixture was then allowed to stir at 70° C. for 18 h. At this point the reaction mixture was allowed to cool to room temperature and then quenched by the addition of ammonium chloride. The mixture was then diluted with DCM, transferred to a separatory funnel and washed with DCM three times. The combined organic layers were then dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting solid compound (38%) was carried onto the next step without further purification.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customquenched by the addition of ammonium chloride
  3. additionThe mixture was then diluted with DCM
  4. customtransferred to a separatory funnel
  5. washwashed with DCM three times
  6. dry with materialThe combined organic layers were then dried over anhydrous Na2SO4
  7. customthe volatiles were removed in vacuo
  8. customThe resulting solid compound (38%) was carried onto the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8fe66a59929a4b21a53bf90333d0f1b5
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315530B2

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