Hydrazine hydrate (1:1) → HCID 24752917, compound

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Reaction Steps

The product from Example 6.8 (0.106 g, 0.254 mmol) was dissolved in 7M NH3-MeOH solution (10 ml), Pd black (106 mg) was added followed by hydrazine hydrate (1.5 ml). The mixture was stirred for 1 h then filtered and the solvent evaporated. The residue was chromatographed on silica gel (CH2Cl2-7M NH3 in MeOH, 85:15) to give (2R,3S)-2-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-4-(methylthio)butane-1,3-diol (0.056 g, 74%) as a colourless solid. [α]D20 −8.4 (c, 0.695, MeOH). 1H NMR (CD3OD) 8.16 (s, 1H), 7.47 (s, 1H), 4.11 (d, j=13.6 Hz, 1H), 3.97 (d, J=13.6 Hz, 1H), 3.84-3.74 (m, 2H), 3.64 (dd, J=11.5, 5.0 Hz, 1H), 2.81 (q, J=5.1 Hz, 1H), 2.72 (dd, J=13.6, 4.7 Hz, 1H), 2.55 (dd, J=13.6, 7.6 Hz, 1H), 2.06 (s, 3H). 13C NMR (CD3OD, referenced to the centre line of CD3OD at 49.0 ppm) δ 152.0, 150.8, 146.5, 129.1, 115.5, 114.9, 71.2, 62.5, 61.8, 42.2, 39.3, 16.0. +ESMS Found 298.1333 (M+H)+ C12H20N5O2S requires 298.1338.

Provenance & Evidence