Reaction Steps
2-[(R)-(2-Amino-1-propyl)amino]benzothiazole trihydrochloride (0.065 g, 70%), m.p. 226-226° C., was subsequently obtained by hydrolysis in a mixture of 6N hydrochloric acid and ethyl acetate (2 ml), the procedure described in Example 1. This 2-[(R)-(2-amino-1-propyl)amino]benzothiazole trihydrochloride (0.06 g, 0. 19 mmol) was reacted with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-di-chloro-9H-purine (0.127 g, 1.2 mmol), followed by deacylation of the purified 2',3',5'-tri-O-acetyl-N-[(R)-1-(2-benzothiazolyl)amino-2-propyl]-2-chloroadenosine using sodium methoxide in methanol (to remove the 2' and 3'-acetyl groups) followed by ethylamine in ethanol, which provided the title N-[(R)-1-(2-benzothiazolyl)amino-2-propyl]-2-chloroadenosine (0.027 g, 29%) as a foam (following column chromatography), 1H NMR (DMSO-d6) δ 1.25 (3H, d, --CHCH3), 3.52-3.70 (4H, m, H-5'a , H-5'b and --CH2 --), 3.94 (1H, q, H-4'), 4.12 (1H, q, H-3'), 4.52 (1H, q, H-2'), 4.53 -4.62 (1H, m, --CHCH3), 5.07 (1H, t, 5'-OH), 5.22, 5.48 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 7.01, 7.22 (2H, 2t, Ar-H), 7.43, 7.66 (2H, 2d, Ar-H), 8.14 (1H, t, N--H), 8.41 (1H, s, H-8), 8.44 (1H, d, N--H). HPLC retention time 10.7 min [gradient elution, 20-80% acetonitrile/water (containing 0. 1% TFA)].
