Imidazole → 5-Amino-3-(5'-o-tert-butyl-dimethylsilanyl-beta-d-ribofuranosyl)-3h-thiazolo[4,5-d]pyrimidin-2-one

HRID 19489

Reaktionsgleichung

Reaktionsgleichung von HRID 19489
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26]C(=O)C)[C@@H:18]([O:19]C(=O)C)[C@H:13]3[O:14]C(=O)C)[C:6]=2[N:7]=1.N1C=CN=C1.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[C@@H:18]([OH:19])[C@H:13]3[OH:14])[C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 116332675-Amino-3-(2',3,5'-tri-O-acetyl-beta-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one

Produkt 1

HCID 667077065-Amino-3-(5'-o-tert-butyl-dimethylsilanyl-beta-d-ribofuranosyl)-3h-thiazolo[4,5-d]pyrimidin-2-oneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 79 (0.68 g, 2.28 mmol) in DMF (10 mL) was added imidazole (0.54 g, 7.93 mmol) and tert-butyldimethylsilyl chloride (0.68 g, 4.56 mmol) sequentially. The reaction mixture was stirred at room temperature for 2 h, at which point it was concentrated and purified by flash column chromatography (silica, MeOH/CHCl3; gradient=5-20%) to afford 0.49 g (52%) 87 as a white solid: 1H (400 MHz, d6-DMSO) δ 8.33 (s, 1H), 6.87 (s, 2H), 5.90 (d, J=4.0 Hz, 1H), 5.33 (d, J=5.6 Hz, 1H), 5.00 (d, J=5.2 Hz, 1H), 4.79 (q, J=5.2 Hz, 1H), 4.16 (q, J=5.2 Hz, 1H), 3.77 (m, 2H), 3.64 (dd, J=12.0, 7.2 Hz, 1H), 0.84 (s, 9H), 0.00 (s, 6H); MS (+)-ES [M+H]+ m/z 415.4.

Aufarbeitung

  1. concentrationwas concentrated
  2. custompurified by flash column chromatography (silica, MeOH/CHCl3; gradient=5-20%)

Quellen und Nachweise

ORD-Eintrag
ord-09e741117e3544bd96272e936487c8e8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745415B2

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