Potassium Carbonate → 5-amino-3-[(2R,3R,5S)-5-(1-hydroxypropyl)-3-prop-2-enyloxolan-2-yl]-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione

HRID 60735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60735
C([O:9][CH:10]([C@@H:13]1[CH2:17][C@@H:16]([CH2:18][CH:19]=[CH2:20])[C@H:15]([N:21]2[C:25]3[N:26]=[C:27]([NH2:31])[NH:28][C:29](=[O:30])[C:24]=3[S:23][C:22]2=[O:32])[O:14]1)[CH2:11][CH3:12])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CO>[CH2:18]([C@@H:16]1[CH2:17][C@@H:13]([CH:10]([OH:9])[CH2:11][CH3:12])[O:14][C@H:15]1[N:21]1[C:25]2[N:26]=[C:27]([NH2:31])[NH:28][C:29](=[O:30])[C:24]=2[S:23][C:22]1=[O:32])[CH:19]=[CH2:20]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 1371087171-[(2S,4R,5R)-4-allyl-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]propyl benzoate2×

Produkt 1

HCID 1371087595-amino-3-[(2R,3R,5S)-5-(1-hydroxypropyl)-3-prop-2-enyloxolan-2-yl]-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dioneAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-[(2S,4R,5R)-4-allyl-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]propyl benzoate (compound 26f, 800 mg, 1.75 mmol) in methanol (25 mL) was added K2CO3 (483 mg, 3.5 mmol). After being stirred at room temperature for 12 hours, the reaction was diluted by saturated NH4Cl solution and extracted with DCM. The organic layers were combined and concentrated in vacuo. The residue was purified by preparative HPLC to afford 200 mg of 3-[(2R,3R,5S)-3-allyl-5-(1-hydroxypropyl)tetrahydrofuran-2-yl]-5-amino-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (Example 26). 100 mg of Example 26 was further separated by supercritical fluid chromatography (SFC) to afford 32.0 mg of Example 26-A and 30.8 mg of Example 26-B as white solid.

Aufarbeitung

  1. extractionextracted with DCM
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-fbbab511873f42c28a60ff46bb78a2a8
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441008B2

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