Ammonium fluoride → 5-Amino-3-[(2R,3R,5S)-3-(1-fluoro-1-methyl-ethyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

HRID 60769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60769
[NH2:1][C:2]1[NH:3][C:4](=[O:40])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[C@H:16]([C:17]([F:20])([CH3:19])[CH3:18])[CH2:15][C@@H:14]([CH2:21][O:22][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[O:13]3)[C:6]=2[N:7]=1.[NH4+].[F-]>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:40])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[C@H:16]([C:17]([F:20])([CH3:19])[CH3:18])[CH2:15][C@@H:14]([CH2:21][OH:22])[O:13]3)[C:6]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 25516Ammonium fluorideHCID 1371902235-amino-3-[(2R,3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(1-fluoro-1-methyl-ethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione2×

Produkt 1

HCID 1371086975-Amino-3-[(2R,3R,5S)-3-(1-fluoro-1-methyl-ethyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dioneAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 5-amino-3-[(2R,3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(1-fluoro-1-methyl-ethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (compound 40h, 66 mg, 0.12 mmol) and NH4F (133 mg, 3.6 mmol) in methanol was heated under reflux for 1.5 hrs. The resulting mixture was concentrated in vacuo and the residue was purified by preparative HPLC to afford 10 mg of 5-amino-3-[(2R,3R,5S)-3-(1-fluoro-1-methyl-ethyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (Example 40) as a white solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hrs
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a4d00bd2e89e427383ca0c2294c38e0b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441008B2

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