Dimethylformamide → HCID 178425937, Verbindung

HRID 1678019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678019
[CH3:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.[H-].[Na+].[Si:16]([O:23][C@@H:24]1[C@H:28]([CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:27][C@@H:26]([O:38][C:39]2[N:47]=[CH:46][N:45]=[C:44]3[C:40]=2[N:41]=[C:42](I)[N:43]3C2CCCCO2)[CH2:25]1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>>[Si:16]([O:23][C@@H:24]1[C@H:28]([CH2:29][O:30][Si:31]([C:34]([CH3:35])([CH3:36])[CH3:37])([CH3:32])[CH3:33])[CH2:27][C@@H:26]([O:38][C:39]2[N:47]=[CH:46][N:45]=[C:44]3[C:40]=2[N:41]=[C:42]([S:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[NH:43]3)[CH2:25]1)([C:19]([CH3:20])([CH3:21])[CH3:22])([CH3:17])[CH3:18]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 79303-ThiocresolHCID 24758Sodium hydrideHCID 667979406-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]-oxy}methyl)cyclopentyl]oxy}-8-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Produkt 1

HCID 178425937HCID 178425937, VerbindungAusbeute 82,1 %

Versuchsvorschrift

To a solution of 3-methylbenzenethiol (0.55 mL, 0.0046 mol) in DMF (10 mL, 0.2 mol) was added sodium hydride (0.093 g, 0.0023 mol). The mixture was stirred at room temperature for 10 minutes and then 6-{[(1R,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl]oxy}-8-iodo-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (400 mg, 0.0006 mol) (Example 115, steps a-b) was added and the solution was heated at 150° C. for 8 hours. The reaction was cooled, quenched by addition of water and the mixture was extracted with ethyl acetate, washed with water, brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 30% ethyl acetate/hexanes) to obtain 296 mg (80%) of the title compound.

Aufarbeitung

  1. temperaturethe solution was heated at 150° C. for 8 hours
  2. temperatureThe reaction was cooled
  3. customquenched by addition of water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (0 to 30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8d6ebea3a6e04adabd6486aeed7cd50b
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008307B2

Notizen zur Reaktion

Wird geladen…