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Sodium hydride → HCID 59841049, Verbindung

HRID 1625159
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1625159
[OH:1][CH:2]([C:4]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:12](=[O:20])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH3:21])[N:5]=1)[CH3:3].[H-].[Na+].Cl[C:25]1[N:33]=[CH:32][N:31]=[C:30]2[C:26]=1[N:27]=[CH:28][N:29]2[CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39]>C1COCC1>[CH3:21][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:12](=[O:20])[N:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:4]([CH:2]([O:1][C:25]1[N:33]=[CH:32][N:31]=[C:30]3[C:26]=1[N:27]=[CH:28][N:29]3[CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH3:3])=[N:5]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydride2×HCID 108698516-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-purine2×HCID 59841037HCID 59841037, Verbindung

Produkt 1

HCID 59841049HCID 59841049, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of compound 181 (0.069 g, 0.25 mmol) in THF (5 mL) was treated with sodium hydride (0.007 g, 0.27 mmol) and stirred for 10 min. A solution of intermediate compound 13 (0.077 g, 0.27 mmol) in THF (1 mL) was added to the reaction mixture. The flask originally containing the intermediate compound 13 was washed with additional THF (1 mL) and the washings were also added to the reaction mixture. The reaction was allowed to proceed, and additional sodium hydride (0.005 g, 0.21 mmol) was added at 21.5 h and 23 h. The reaction was quenched after a total of 24 h by addition of saturated ammonium chloride solution (5 mL). The mixture was extracted with dichloromethane (3×5 mL), and the combined organic extracts were dried over MgSO4. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography (1:1 EtOAc: hexanes→3:2 EtOAC:hexanes) to give compound 182. ESI-MS m/z=529 (MH+). The reaction described above and compound 182 are shown below.

Aufarbeitung

  1. washwas washed with additional THF (1 mL)
  2. additionthe washings were also added to the reaction mixture
  3. customThe reaction was quenched after a total of 24 h
  4. additionby addition of saturated ammonium chloride solution (5 mL)
  5. extractionThe mixture was extracted with dichloromethane (3×5 mL)
  6. dry with materialthe combined organic extracts were dried over MgSO4
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by flash chromatography (1:1 EtOAc: hexanes→3:2 EtOAC:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e10ebd0659d84fe99a22e9f2397cc56e
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08779131B2

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