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Sodium hydride → HCID 131717242, Verbindung

HRID 1729404
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1729404
[H-].[Na+].[Cl:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[NH:6][C:7]([CH2:13][CH2:14][CH3:15])=[N:8]2.[C:16]([O:20][C:21]([C:23]1[C:24]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35]Br)=[CH:31][CH:30]=2)=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C>[Cl:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[N:6]=[C:7]([CH2:13][CH2:14][CH3:15])[N:8]2[CH2:35][C:32]1[CH:33]=[CH:34][C:29]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])=[CH:30][CH:31]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 190122236-Chloro-8-propylpurine

Produkt 1

HCID 131717242HCID 131717242, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a suspension of NaH (0.20 g) in dry DMF (3 ml), 6-chloro-8-propyl-purine (0.06 g, 0.3 mmol) was added, and the mixture was stirred at 40° C. for 20 minutes. t-Butyl-4-bromomethylbiphenyl-2'-carboxylate (0.11 g, 0.31 mmol) was then added at room temperature and stirring continued for 3 hours at 40° C. The content of the flask was poured into ice-water (100 ml and extracted with ethylacetate. The organic phase was separated and dried over MgSO4. Removal of the solvent under reduced pressure gave the crude product which was then purified by flash-chromatography on silica-gel using ethylacetate-hexane (1:1). The pure titled compound was obtained as a glass-like solid (0.073 g, 53%). NMR (CDCl3): δ 1.04 (t, J=9 Hz, 3H), 1.213 (s, 9H), 1.91 (m, 2H), 2.89 (t, 2H), 5.52 (s, 2H), 7.15-7.52 (m, 7H), 7.79 (dd, J1 =8 Hz and J2 =2 Hz, 1H), 8.72 (s, 1H); FAB-MS: m/e 463 and 465 (M+H).

Aufarbeitung

  1. additionwas added
  2. stirringstirring
  3. waitcontinued for 3 hours at 40° C
  4. extractionextracted with ethylacetate
  5. customThe organic phase was separated
  6. dry with materialdried over MgSO4
  7. customRemoval of the solvent under reduced pressure
  8. customgave the crude product which
  9. customwas then purified by flash-chromatography on silica-gel

Quellen und Nachweise

ORD-Eintrag
ord-ef65e44d4ee64f52967555881ac4f208
Quelldatensatz
uspto-grants-1994_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05332744

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