Hydrochloric Acid → HCID 57236764, compound

Participants

Reaction Steps

Sodium hydride (60% oil dispersion, 113 mg was added to cyclopentanol (7 mL). To the resulting solution, after effervescence had ceased, was added (+)-(1S-2R-4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol (400 mg, 1.4 mmol). The solution was maintained at 85° for 40 minutes, cooled to room temperature, and neutralized with 1N hydrochloric acid. Volatiles were removed and the residue chromatographed on silica gel. Title compound was eluted with methanol:chloroform/15:85 as a white solid foam which solidified form acetonitrile:methanol/20:1 as a white powder (223 mg, 48%), m.p. 181-182°; mass spectrum (Cl, CH4): 334(M+1); 1H-NMR (DMSO-d6)δ: 7.97 (s, 1, H8), 6.32 (br s, 2, NH2), 5.60 (m, 1, CHO of cyclopentyl) 5.0-4.8 (m, 1, CHN), 4.78 (d, J=4.1 Hz, 1, OH), 4.66 (t, J=5.1 Hz, 1, CH2OH), 4.1 (m, 1, CHOH), 3.6-3.4 (m, 2, CH2O), 2.4-1.9 (m, 6 methylene), 1.9-1.5 (m, 7, methylene); [α]20589 +9.34°, [α]20578 +9.85°, [α]20546 +11.1°, [α]20430 +18.2°, [α]20365 +26.6° (c=0.782, methanol).

Provenance & Evidence