Dimethylformamide → N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]-2-(dimethylamino)adenosine

Participants

Reaction Steps

The title compound was prepared according to general method B by reaction of N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]-2-chloroadenosine (1.02 g, 2.0 mmol) (Example 5)in dimethylformamide (10 ml) to provide the desired N-[(R)-1-(2-benzothiazolyl)thio-2-propyl]-2-(dimethylamino )adenosine (0.12 g, 12%) as a foam (following column chromatography), 1H NMR (DMSO-d6) δ 1.38 (3H, d, --CHCH3), 2.92 (6H, s, --N(CH3)2), 3.40-3.72 (4H, m, H-5'a and H-5'b and --CH2 --), 3.88 (1H, q, H-4'), 4.15 (1H, q, H-3'), 4.65 (1H, q, H-2'), 4.72-4.85 (1H, m, --CH--), 4.89 (1H, t, 5'-OH), 5.14, 5.36 (2H, 2d, 2'- and 3'-OH), 5.75 (1H, d, H- 1'), 7.35, 7.46 (2H, 2 t, Ar-H), 7.50 (1H, d, N--H), 7.84, 7.99 (2H, 2d, Ar-H), 7.94 (1H, s, H-8). HPLC retention time 16.8 min [gradient elution, 20-80% acetonitrile/water (containing 0. 1% TFA)].

Provenance & Evidence