The Synthesis of Aminopyri Dine-Based Phosphonoacetates as ADP Analogs

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• For the major diol isomen mp 180–182°C: R1 0.15 (10% melhanol/chloroform- the synisomer has R1 0.18); IR (mull) 3511, 2954, 2925, 2870, 2855, 1624, 1546, 1336, 1190, 1100 cm−1 1H NMR (300 MHz, pyridine-d5) 8.42 (broad d, 1 H, J = 7.6 Hz, N-H), 7.93 (d, 1 H, J = 3.0 Hz, aromatic H), 7.90 (d, 1 H, J = 2.9 Hz, aromatic H), 7.03 (broad s, 1 H, O-H), 6.70 (broad s, 1 H, O-H), 6.60 (broad s, 1 H, O-H), 4.64 (t, 1 H, J = 4.7 Hz, 0-CH), 4.48 (t, 1H, J = 5.7 Hz, O-CH), 4.39 (m, 1 H, N-CH), 4.10 (dd, 1 H, J = 10.7 Hz, J = 4.4 Hz, O-CH2a), 4.05 (dd, 1 H, J = 10.4 Hz, J = 4.3 Hz, O-CH2b, 2.85–2.65 (m, 2 H, CH & CH2a, 1.94 (m, 1H, CH2b 13C NMR(75.5 MHz, pyridine-d5 149.5, 141.1, 129.0,107.7,96.4, 76.2, 72.1,61.2, 57.0,44.5,28.8; Anal. Calcd for CnH14BrN3O6: C, 36.28; H, 3.87; N, 11.54. Found: C, 36.50; H, 3.78; N, 11.37. HRMS (FAB) Calcd for C11H15BrN3O6: 364.0145. Found: 364.0141
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• This material is the monocyclohexylammonium salt of the acetonide of 12
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• For the diol-phosphonate derived from 13: Rf 0.24 (4:1:1 acetonitrile/water/concentrated aqueous ammonium hydroxide); 1H NMR (300 MHz, D2O) 7.42 (d, 1 H, J = 2.7 Hz, aromatic H), 7.14 (d, 1 H, J = 2.7 Hz, aromatic H), 4.21 (m, 1 H, O-CH2), 4.1–3.9 (m, 3 H, O-CH's & N-CH), 3.02 (d, 2 H, J = 21.1 Hz, P-CH2), 2.5–2.3 (m, 2 H, CH2a. & CH), 2.48 (s, 3 H, S-CH3), 1.42 (dt, 1 H, J = 13.1 Hz, J = 8.8 Hz, CH2b): 13C NMR (75.5 MHz, D2O) 169.4 (d, J = 6.0 Hz), 154.9, 150.0, 147.0, 100.4, 95.9, 76.4, 72.2, 66.3, 56.8, 41.3, 35.7 (d, J = 125 Hz), 29.1, 13.5; Anal. Calcd for C14H20N3O10PS: 454.0685. Found: 454.0698
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