Réaction #1596986

Équation de réaction

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

Solvants

methanol

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source