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Laboratory for Drug Design and Synthesis, Department of Chemistry & Biochemistry, University of Maryland, Baltimore County, 1000 Hilltop Circle, Baltimore, MD 21250, USA
Nabi, 12280 Wilkins Avenue, Rockville, MD 20852, USA
Author to whom correspondence should be addressed.
Molecules 2001, 6(12), M264;
Received: 8 June 2001 / Accepted: 15 December 2001 / Published: 20 December 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 06 m264 i001
The starting methyl 1-(2’-deoxy-β-d-ribofuranosyl)imidazole-4,5-dicarboxylate (1) was prepared by deoxygenation of the corresponding riboside, employing the literature procedure [1]. To a solution of 1 (150 mg, 0.5 mmol) and guanidine hydrochloride (240 mg, 2.5 mmol) in 30 mL of absolute methanol was added 1 mL of 25% (w/v) sodium methoxide solution in methanol. The reaction mixture was stirred for 24 h at room temperature, then 1 g of silica gel was added. The resulting mixture was evaporated to dryness and the product was isolated by silica gel flash chromatography. The column was successively eluted with chloroform/methanol (10:1) and methanol. The proper fraction was collected and evaporated to afford title product 2 as a colorless solid. Yield 110 mg (74.5%).
M.p. >250 oC.
1H NMR (DMSO-d6): δ 10.65 (brs, 1H, NH, exchangeable with D2O), 8.47 (s,1H, imidazole), 7.62 (brs, 1H, NH, exchangeable with D2O), 6.65 (t, 1H, J=5.7 Hz, 1H), 6.54 (brs, 1H, NH, exchangeable with D2O), 5.27 (d, 1H, J=4.5 Hz, OH, exchangeable with D2O), 5.09 (t, 1H, J=4.8 Hz, OH, exchangeable with D2O), 4.24 (m, 1H, 4H), 3.84 (m, 1H, 3H), 3.60 (m, 2H, 5H), 2.18 (dt, 1H, J=13.5 and 5.7 Hz, 2H), 2.02 (d, 1H, J=13.5 Hz, 2H).
HRMS (FAB): C11H14N5O5 (MH+): Calcd., 296.0995; Found, 296.0994.
Anal. Calcd. For C11H13N5O5.0.25 H2O: C, 44.09; H, 4.51; N, 23.37. Found: C, 44.08; H, 4.54; N, 23.36.

Supplementary materials

Supplementary File 1Supplementary File 2


  1. Chen, H. -M.; Hosmane, R. S. Molecules 2000, 5, 1187–1193.
  • Sample Availability: Available from the authors and from MDPI.
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