Reaction #56636

Reaction equation

2,5,6-Trichloro-3-cyano-1-(β-D-ribofuranosyl)indole

hydrazine hydrate

→

4.37

Yield 90.0%

5,6-Dichloro-3-amino-8-(β-D-ribofuranosyl)pyrazolo[3,4-b]indole

Yield 90.0%

Solvents

water

Conditions

Workup

1. 1
   OtherThe suspension thus obtained
2. 2
   Temperaturecooled to 0 □C
3. 3
   Filtrationthe suspension filtered
4. 4
   Washthe solids rinsed with water
5. 5
   OtherThe solids were recrystallized from MeOH/H2O

Procedure

2,5,6-Trichloro-3-cyano-1-(β-D-ribofuranosyl)indole (4.4, 102 mg, 0.27 mmol) was dissolved in hydrazine hydrate (2 mL), and the resulting solution was stirred at room temperature for 30 min. The suspension thus obtained was diluted with water (8 mL), cooled to 0 □C, and the suspension filtered and the solids rinsed with water. The solids were recrystallized from MeOH/H2O to yield 91 mg (90%) of 4.37 as a white crystalline solid: mp 198-201 □C; Rf 0.3 (20% MeOH/CHCl3); 1H-NMR (500 MHz, DMSO-d6): δ 8.68 (s, 1H, D2O exch.), 7.76 (s, 1H), 7.27 (s, 1H), 5.81 (d, 1H), 5.78 (b, 1H, D2O exch.), 5.31-5.28 (m, 2H, D2O exch.), 4.84 (s, 2H, D2O exch.), 4.27 (q, 1H), 4.07 (s, 1H), 4.00 (s, 1H), 3.68 (q, 2H). 13C-NMR (125 MHz, DMSO-d6): δ 155.50, 131.99, 129.00, 123.60, 121.60, 116.91, 115.45, 111.96, 88.32, 85.95, 71.06, 69.95, 63.28, 60.78. HRMS (EI) m/z calcd. for C14H14Cl2N4O4 372.0392, found 372.0397. Anal calcd for C14H14Cl2N4O4·¼H2O: C, 44.52; H, 3.87; N, 14.83. Found: C, 44.63; H, 4.10; N, 14.72.

Source