反应详情

Acetyl chloride (0.117 ml, 1.65 mmol) was added to a stirred solution of 2-aminopropane-1,3-diol (0.3 g, 3.29 mmol) and 5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde (0.196 g, 0.659 mmol, prepared as in G. B. Evans, R. H. Furneaux, A, Lewandowicz, V. L. Schramm and P. C. Tyler, J. Med. Chem., 2003, 46, 3412) in MeOH (5 ml). Sodium cyanoborohydride (0.062 g, 0.988 mmol) was added and the mixture was stirred at rt overnight. The solvent was evaporated and the residue chromatographed on silica gel (CH2Cl2-MeOH-28% NH4OH, 95:5:0.5 then 9:1:0.05) to give 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-propane-1,3-diol (0.188 g, 77%) as a colourless solid. 1H NMR (CD3OD) δ 8.42, (s, 1H), 7.65 (s, 1H), 7.25-7.16 (m, 5H), 5.75 (s, 2H), 4.50 (s, 2H), 4.10 (s, 3H), 4.03 (s, 2H), 3.68 (dd, J=11.2, 5.9 Hz, 2H), 3.58 (dd, J=11.2, 5.9 Hz, 2H), 2.81 (pentet, J=5.6 Hz, 1H). 13C NMR (CD3OD, 75.5 MHz, referenced to centre line of CD3OD at δ 49.0) δ 157.9, 150.8, 150.6, 138.7, 134.1, 129.3, 128.8, 128.6, 117.0, 116.2, 78.5, 71.5, 62.5 (CH2X2), 61.3, 54.3, 41.4. +ESMS Found 373.1865 (M+H)+ C19H25N4O4 requires 373.1876.

1. custom0.196 g, 0.659 mmol, prepared as in G
2. customThe solvent was evaporated
3. customthe residue chromatographed on silica gel (CH2Cl2-MeOH-28% NH4OH, 95:5:0.5