Reacción #1596986

Ecuación de reacción

42

7-Allyl-2-amino-9-(2′,3′,5′-tri-O-acetyl-β-D-ribofuranosyl)-7,9-dihydro-purin-8-one

K2CO3

→

7-Allyl-2-amino-9-β-D-ribofuranosyl-7,9-dihydro-purin-8-one

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONTo the cloudy mixture was added Amberlite
2. 2
   workup.STIRRING(0.5 g) and stirred till neutral and
3. 3
   Filtraciónfiltered
4. 4
   ConcentraciónThe filtrate was concentrated
5. 5
   Otroto give an off-white solid, which
6. 6
   Lavadowas washed with water
7. 7
   Otrodried under high vacuum
8. 8
   Otroto give 93.5 mg of pure 43 in quantitative yield as an off white solid

Procedimiento

To a solution of 42 (0.13 g, 0.29 mmol) in methanol (4 mL) was added solid K2CO3 (0.024 g, 0.17 mmol) and the reaction stirred at ambient temperature for 18 h. To the cloudy mixture was added Amberlite CG-50 (0.5 g) and stirred till neutral and filtered. The filtrate was concentrated to give an off-white solid, which was washed with water and dried under high vacuum to give 93.5 mg of pure 43 in quantitative yield as an off white solid: 1H NMR (400 MHz, d6-DMSO) δ 7.88 (s, 1H), 6.33 (br s, 2H), 5.85 (m, 1H), 5.66 (d, J=6.0 Hz, 1H), 5.30 (d, J=5.6 Hz, 1H), 5.20 (s, 1H), 5.16 (d, J=8.4 Hz, 1H), 5.01 (d, J=4.8 Hz, 1H), 4.89 (q, J=5.6 Hz, 1H), 4.75 (br s, 1H), 4.35 (d, J=5.2 Hz, 2H), 4.10 (t, J=8.4 Hz, 1) 3.80 (q, J=3.6 Hz, 1H), 3.57 (m, 1H), 3.44 (m, 1H). MS (+)-ES [M+H]+ 324.1 m/z.

Fuente