B(Br)(Br)Br.C([O:12]C[N:14]1[C:22]2[C:21]([O:23]C)=[N:20][CH:19]=[N:18][C:17]=2[C:16]([CH2:25][NH:26][C:27]([CH2:32][OH:33])([CH2:30][OH:31])[CH2:28][OH:29])=[CH:15]1)C1C=CC=CC=1>ClCCl.CO>[NH4+:14].[OH-:12].[OH:23][C:21]1[C:22]2[NH:14][CH:15]=[C:16]([CH2:25][NH:26][C:27]([CH2:30][OH:31])([CH2:32][OH:33])[CH2:28][OH:29])[C:17]=2[N:18]=[CH:19][N:20]=1Boron tribromide (1 mL, 1.0 mmol) was added dropwise to a solution of 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(hydroxymethyl)propane-1,3-diol (30 mg, 74.5 μmol) in dichloromethane (5 mL) and stirred at r.t. A white solid precipitated from the reaction after 1 h and the reaction was then quenched with methanol, concentrated in vacuo and co-distilled with methanol (3×25 mL) to afford a crude residue. The residue was dissolved in methanol absorbed onto silica and chromatographed eluting with 5:4.5:0.5 DCM:MeOH:NH4OH to afford 2-((4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(hydroxymethyl)propane-1,3-diol (7 mg, 26.1 μmol, 35.0% yield) as a white solid which was converted to the HCl salt for NMR analysis. Mpt 223-224° C. (plates from EtOH). 1H NMR (D2O, referenced to internal acetone at 2.225 ppm) δ 9.06, (s, 1H), 7.92 (s, 1H), 4.59 (s, 2H), 3.91 (s, 6H). 13 NMR (D2O, referenced to internal acetone at δ 31.5) δ 153.7, 146.0, 134.2, 133.0, 119.4, 104.7, 67.6, 59.3, 36.4. +ESMS Found 269.1263 (M+H)+ C11H17N4O4 requires 269.1250.
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