Hydrochloric Acid → HCID 57083073, compound

Participants

Reaction Steps

(+)-(1S, 2R, 4R)-4-(2-Amino-1,6-dihydro-6-thioxo-9H-purin-9-yl)-2-(hydroxymethyl)-1-cyclopentanol (351 mg, 1.25 mmol) and 1N sodium hydroxide (1.15 mL) were stirred with allyl chloride (0.15 mL) for 5 hour. The solution was neutralized with hydrochloric acid and volatiles evaporated. The residue was chromatographed on silica gel. Title compound was eluted with 12% methanol-chloroform as a white solid foam which solidified to white powder from acetonitrile (240 mg, 60%): m.p. 133°-134°; mass spectrum (cl, CH4):322 (M+1); 1H-NMR (DMSO-d6) δ: 8.07 (s, 1, H8), 6.51 (br s, 2, NH2), 6.10-5.85 (m, 1, CH=), 5.45-5.30 (m, 1, 1/2CH2 =), 5.15-5.05 (m, 1, 1/2CH2 =), 5.0-4.8 (m, 1, CHN), 4.79 (d, J=4.1 Hz, 1, OH), 4.66 (t, J=5.2 Hz, 1, CH2OH), 4.15-4.0 (m, 1, CHO), 3.98 (d, J=6.9 Hz, 2, CH2S), 3.6-3.4 (m, 2, CH2O), 2.4-1.9 (m, 4, CH+methylenes), 1,75-1.55 (m, 1, 1/2CH2); [α]20589 +9.30°, [α]20578 +9.68°, [α]20546 +11.1°, [α]20436 +18.6°, [α]20365 +25.4° (c=0.79, methanol).

Provenance & Evidence