Ammonia → 2-chloro-N[(R)-1-(1-methyl-2-imidazolyl)thio-2-propyl]adenosine

Participants

Reaction Steps

The title compound was prepared according to method A as described above in Example 1 by reacting (R)-1-(1-methyl-2-imidazolyl)thio-2-propylamine hydrochloride [prepared using the same method as described in Example 1 from 2-mercapto-1-methylimidazole (3.31 g, 29 mmol) and 2-[(R)-N-tert-butyloxycarbonyl]amino-1-propanol (5.08 g, 29 mmol) followed by acidic hydrolysis] (2.30 g, 11.1 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.46 g, 5.5 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N[(R)-1-(1-methyl-2-imidazolyl)-thio-2-propyl]adenosine (1.1 g, 43%) as a foam after column chromatography. 1H NMR (DMSO-d6) δ 1.28 (3H, d, --CHCH3), 3.53-3.60 (1 H, m, H-5'a), 3.63-3.70 (1H, m, H-5'b), 3.95 (1H, q, H- 4'), 4.13 (1H, q, H-3'), 4.51 (1 H, q, H-2'), 5.07 (1H, t, 5'-OH), 5.22, 5.50 (2H, 2d, 2'- and 3'-OH), 5.82 (1H, d, H-1'), 6.92 (1H, s, Ar-H) 7.20 (1H, s, Ar-H), 8.40 (1H, s, H-8), 8.55 (1H, s, N--H). HPLC retention time 19.3 min [gradient elution, 20-80% acetonitrile/water (containing 0.1% TFA)].

Provenance & Evidence