Reaction #1596986

Reaction equation

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

Solvents

methanol

Conditions

Workup

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
   Otherto give an off-white solid, which
6. 6
   Washwas washed with water
7. 7
   Otherdried under high vacuum
8. 8
   Otherto give 93.5 mg of pure 43 in quantitative yield as an off white solid

Procedure

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