Sodium hydride → 6-{[(1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl]oxy}-8-(1-naphthyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

HRID 1747596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747596
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:19]1[N:27]=[CH:26][N:25]=[C:24]2[C:20]=1[N:21]=[C:22]([C:34]1[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[CH:36][CH:35]=1)[N:23]2[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1>CN(C=O)C>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C@H:12]([O:15][C:19]2[N:27]=[CH:26][N:25]=[C:24]3[C:20]=2[N:21]=[C:22]([C:34]2[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[CH:37]=[CH:36][CH:35]=2)[N:23]3[CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 66797963(1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentanolHCID 866187096-chloro-8-(1-naphthyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Produkt 1

HCID 667978956-{[(1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl]oxy}-8-(1-naphthyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of (1S,3S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-cyclopentanol (111.0 mg, 0.0004817 mol) (azeotroped with toluene) in DMF (3.6 mL) at 0° C. under an atmosphere of nitrogen was added sodium hydride (24.1 mg, 0.000602 mol). The mixture was stirred for 15 min. To this cold solution was added a solution of 6-chloro-8-(1-naphthyl)-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (163 mg, 0.000401 mol) in DMF (1.8 mL). The flask was rinsed with DMF (1.0 mL)) and this was added to the reaction as well. The resulting mixture was stirred for 20 h. The reaction mixture was quenched with water and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and collected in vacuo. The residue was purified by flash chromatography (10 to 40% EtOAc/hexanes) to obtain 156.9 mg (70%) of the title compound as a white solid.

Aufarbeitung

  1. washThe flask was rinsed with DMF (1.0 mL)) and
  2. additionthis was added to the reaction as well
  3. stirringThe resulting mixture was stirred for 20 h
  4. customThe reaction mixture was quenched with water
  5. extractionthe mixture was extracted with EtOAc (3×)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customcollected in vacuo
  9. customThe residue was purified by flash chromatography (10 to 40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-bfbd084221a54d8fb6313c140f93c29e
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150525B2

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