Hydrochloric Acid → (1S,2R,5S)-5-(8-Aminoimidazo[1,2-a]pyrazin-3-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol

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Reaction Conditions

Reaction Steps

Concentrated HCl solution (0.6 mL) was added to 3-((3aS,4S,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)imidazo[1,2-a]pyrazin-8-amine (1-9) (130 mg, 0.239 mmol, 1 equiv) in methanol (3 mL) and heated to 65° C. After 2 hours the mixture was cooled to 23° C. C and purified via reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present) to afford (1S,2R,5S)-5-(8-aminoimidazo[1,2-a]pyrazin-3-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol (1-10) as an amber solid. 1H NMR (500 MHz, CD3OD) δ 8.04 (d, 1H, J=5.5 Hz), 7.62 (s, 1H), 7.24 (d, 1H, J=5.5 Hz), 5.93 (s, 1H), 4.51 (d, 1H, J=5.5 Hz), 4.31 (m, 2H), 4.23 (br m, 1H), 4.10 (t, 1H, J=5.5 Hz). LRMS m/z (M+H) 263.1 found, 263.1 required.

Provenance & Evidence