Reacción #56636

Ecuación de reacción

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

hydrazine hydrate

→

4.37

Rendimiento 90.0%

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

Rendimiento 90.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe suspension thus obtained
2. 2
   Temperaturacooled to 0 □C
3. 3
   Filtraciónthe suspension filtered
4. 4
   Lavadothe solids rinsed with water
5. 5
   OtroThe solids were recrystallized from MeOH/H2O

Procedimiento

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.

Fuente