Sodium sulfide nonahydrate → HCID 178481608, Verbindung

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Reaktionsgleichung

Br[C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH2:22][O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[C:6](=[O:30])[N:5]([CH3:31])[C:4]=2[N:3]=1.O.O.O.O.O.O.O.O.O.[S-2:41].[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C.O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:10]2[C:9]3[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH2:22][O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)[C:6](=[O:30])[N:5]([CH3:31])[C:4]=3[N:3]=[C:2]2[SH:41])=[CH:13][CH:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

To a solution of 8-bromo-7-(4-chlorobenzyl)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (400 mg, 0.781 mmol, intermediate 14) in DMF (10 mL) was added sodium sulfide nonahydrate (375 mg, 1.563 mmol). The reaction was stirred at 85° C. for 16 h. The mixture was cooled, diluted with ethyl acetate and water, and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 7-(4-chlorobenzyl)-8-mercapto-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (230 mg, 63.4%) as orange oil. LCMS retention time 1.517 min; LCMS MH+-THP 381.

Aufarbeitung

temperatureThe mixture was cooled
customthe phases were separated
washThe organic phase was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-923cfb35107647b6b038c82ff0ff3dad
Quelldatensatz: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09359359B2

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