Hydrochloric Acid → 9-(2-Cyclohexenyl)-2-ethoxy-9H-adenine

Reaction equation

Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]2)=[C:4]([NH2:17])[N:3]=1.[O-:18][CH2:19][CH3:20].[Na+].Cl>C(O)C>[CH:11]1([N:8]2[CH:7]=[N:6][C:5]3[C:9]2=[N:10][C:2]([O:18][CH2:19][CH3:20])=[N:3][C:4]=3[NH2:17])[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]1

Participants

Procedure

A mixture of 2-chloro-9-(2-cyclohexenyl)-9H-adenine (310 mg., 1.24 mmole) and a solution of sodium ethoxide in ethanol (0.25-1 N, ~10 ml.) was refluxed overnight under an atmosphere of nitrogen. The reaction mixture was poured into ice-water, neutralized with 1 N HCl and extracted with ethyl acetate (20 ml.). The extracts were washed with water, dried over Na2SO4 and filtered. The filtrate was evaporated and the residue then subjected to silica gel chromatography (silica gel 7 g., eluted with 1% CH3OH--CHCl3) to give the title product in 92% yield; m.p. 67°-72° C. IR(KBr): 3320, 2940, 1640, 1595, 1465, 1410, 1385, 1340 cm-1. UV: λmaxEtOH 254 nm(ε8400), 269 nm(ε12600). NMR(CDCl3): 1.44 (3H, t, J=7 Hz), 2.00(6H, m), 4.45(2H, q, J=7 Hz), 5.20(1H, m), 5.95(2H, m), 6.16(2H, s), 7.62(1H, s).