Reaction #1596991

Reaction equation

AcOH

89

5-Amino-3-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-3H-thiazolo[4,5-d]pyrimidin-2-one

K2CO3

→

compound 90

Yield 90.1%

5-Amino-3-β-D-ribofuranosyl-3H-thiazolo[4,5-d]pyrimidin-2-one

Yield 90.1%

Solvents

MeOH

Conditions

Workup

1. 1
   workup.STIRRINGThe resulting mixture was stirred at room temperature for additional 30 min
2. 2
   Concentrationconcentrated
3. 3
   Othertriturated with H2O (2 ml)

Procedure

To a solution of 89 (0.52 g, 1.22 mmol) in MeOH (20 mL) was added K2CO3 (25 mg, 0.18 mmol). The reaction was stirred at room temperature overnight, then neutralized with AcOH (21 μL, 0.36 mmol). The resulting mixture was stirred at room temperature for additional 30 min, concentrated, and triturated with H2O (2 ml) to afford 0.33 g of compound 90 (89%) as a white solid: mp 220° C. (Dec); 1H (400 MHz, d6-DMSO) δ 8.34 (s, 1H), 6.85 (s, 2H), 5.90 (d, J=4.8 Hz, 1H), 5.31 (d, J=5.6 Hz, 1H), 4.98 (d, J=5.6 Hz, 1H), 4.81 (q, J=5.2 Hz, 1H), 4.67 (t, J=6.0 Hz, 1H), 4.11 (q, J=5.2 Hz, 1H), 3.77 (dd, J=10.8, 4.8 Hz, 1H), 3.58 (m, 1H), 3.44 (m, 1H); MS (+)-ES [M+H]+ m/z 301.1. Elemental Analysis calc'd for C10H12N4O5S.0.3 H2O: C, 39.29; H, 4.15; N, 18.33; S 10.49. Found: C, 39.51; H, 4.18; N, 17.95; S, 10.27.

Source