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Cyclopentanol → 1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-8-(cyclopentyloxy)-3-methyl-1H-purine-2,6(3H,7H)-dione

HRID 2200741
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Reaktionsgleichung

Reaktionsgleichung von HRID 2200741
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:10]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[C:17]2[C:16](=[O:27])[N:15]([CH2:28][CH2:29][CH2:30][O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C:14](=[O:39])[N:13]([CH3:40])[C:12]=2[N:11]=1>C1COCC1.O>[Si:32]([O:31][CH2:30][CH2:29][CH2:28][N:15]1[C:16](=[O:27])[C:17]2[N:18]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[C:10]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:11][C:12]=2[N:13]([CH3:40])[C:14]1=[O:39])([C:35]([CH3:36])([CH3:37])[CH3:38])([CH3:33])[CH3:34]
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Komponenten

6

Edukt 3

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 904028568-bromo-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione2×

Produkt 1

HCID 904026851-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-8-(cyclopentyloxy)-3-methyl-1H-purine-2,6(3H,7H)-dioneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Step 1 Cyclopentanol (0.21 mL, 2.31 mmol) was dissolved in THF (5 mL) and sodium hydride (60% in oil, 0.092 g, 2.31 mmol) was added. The reaction was stirred for 1 h. 8-Bromo-1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.25 g, 0.46 mmol, intermediate 77) was added and the reaction was stirred at room temperature for 15 h. The reaction was diluted with water (100 mL) and extracted with ethyl acetate (3×75 mL). The combined extracts were dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure to give 1-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-(4-chlorobenzyl)-8-(cyclopentyloxy)-3-methyl-1H-purine-2,6(3H,7H)-dione (0.25 g, 100% yield) as a golden oil. LCMS retention time=5.843 min and 71% purity, LCMS MH+ 547.

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature for 15 h
  2. extractionextracted with ethyl acetate (3×75 mL)
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-166b2c829d7945f4a2db33bf11edee50
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09359359B2

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