Reaction #577235

Reaction equation

17

Acetic acid 6-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-2,2-di-tert-butyl-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-7-yl ester

Pyridine

→

18

Yield 90.8%

Acetic acid 2-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester

Yield 90.8%

Solvents

methanol

Conditions

Workup

1. 1
   ConcentrationThe mixture was concentrated
2. 2
   Otherpurified by flash chromatography (0-10% MeOH—CH2Cl2)

Procedure

To a solution of 17 (2.28 g, 4.73 mmol) in 10 mL anhydrous methanol was added 327 μL HF/Pyridine. The reaction was stirred at room temperature for 1 hour. The mixture was concentrated and purified by flash chromatography (0-10% MeOH—CH2Cl2) yielding 1.47 g (90%) 18: 1H NMR (400 MHz, DMSO-d6) δ 8.38 (1H, s), 6.86 (2H, bs), 5.82 (1H, d, J=4.68 Hz), 5.76-5.78 (1H, m), 5.34 (1H, d, J=7.8 Hz), 4.60 (1H, t, J=5.46 Hz), 4.27-4.31 (1H, m), 3.96-4.00 (1H, m), 3.61-3.72 (2H, m), 2.03 (3H, s); [M]+ @ m/z 343.3.

Source