9-(2-cyclohexenyl)-2-propoxy-9H-adenine → 9-Cyclohexyl-2-n-propoxy-9H-adenine
Reaction equation
[CH:1]1([N:7]2[CH:15]=[N:14][C:13]3[C:8]2=[N:9][C:10]([O:17][CH2:18][CH2:19][CH3:20])=[N:11][C:12]=3[NH2:16])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1>C(O)C>[CH:1]1([N:7]2[CH:15]=[N:14][C:13]3[C:8]2=[N:9][C:10]([O:17][CH2:18][CH2:19][CH3:20])=[N:11][C:12]=3[NH2:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2.21 g. (7.8 mmoles) of 9-(2-cyclohexenyl)-2-n-propoxy-9 H-adenine in 30 ml. of 90% ethanol was hydrogenated overnight with 250 mg. of 10% Pd-C and then filtered. The filtrate was evaporated in vacuo, giving a residue which was crystallized from ethyl acetate-n-hexane. Yield 1.85 g. (76%); m.p. 148°-150° C. IR(KBr): 3510, 2930, 1670, 1640, 1595, 1405 cm-1. UV: λmaxMeOH 252 nm(ε8360), 269 nm(ε13200). NMR(CDCl3): δ1.03 (3H, t, J=7 Hz), 1.80(12H, m), 4.20(2H, t, J=7 Hz), 4.35(1H, m), 6.02(2H, s), 7.55(1H, s).
Workup
- filtrationof 10% Pd-C and then filtered