Hydrochloric Acid → 6-[(2,2-diphenylethyl)amino]-9-(tetrahydro-2H-pyran-2-yl) 9H-purine-2-carboxylic acid

HRID 2184277

Reaktionsgleichung

Reaktionsgleichung von HRID 2184277
[C:1]1([CH:7]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([O:21]CC)=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Na+].Cl>ClCCl>[C:30]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([OH:21])=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 21978293Ethyl 6-[(2,2-diphenylethyl)amino]-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carboxylate

Produkt 1

HCID 224759666-[(2,2-diphenylethyl)amino]-9-(tetrahydro-2H-pyran-2-yl) 9H-purine-2-carboxylic acidAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of ethyl 6-[(2,2-diphenylethyl)amino]-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carboxylate (0.55 g, 1.16 mmol) (Preparation 27) in industrial methylated spirits (2.2 ml) was added deionised water (0.08 ml) followed by 10 M aqueous sodium hydroxide solution (0.23 ml, 2.3 mmol). The resultant mixture was stirred at 65° C. for 30 minutes and then at ambient temperature for 18 hours during which time a thick paste was formed. To this mixture was added dichloromethane (10 ml) and the pH was adjusted to 2 by the addition of dilute aqueous hydrochloric acid solution. The phases were separated and the aqueous layer was extracted with dichloromethane (10 ml). The combined organic phases were then dried (MgSO4) and the solvent was removed under reduced pressure to give the title compound as a tan coloured foam (0.43 g) that was identical by 1H-NMR, high performance liquid chromatography, mass spectrometry and thin-layer chromatography to the compound prepared in Preparation 21.

Aufarbeitung

  1. customat ambient temperature for 18 hours during which time a thick paste was formed
  2. customThe phases were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (10 ml)
  4. dry with materialThe combined organic phases were then dried (MgSO4)
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e486f1fec2da4c259963ca371edee487
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900309B1

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