Bromotrimethylsilane → 2-Amino-6-chloro-9-[2-(phosphonomethoxy)ethoxy]purine
반응식
[Cl:1][C:2]1[N:10]=[C:9]([NH:11]C=O)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[O:14][CH2:15][CH2:16][O:17][CH2:18][P:19]([O:24]CC)([O:21]CC)=[O:20].C[Si](Br)(C)C>CN(C)C=O>[NH2:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[O:14][CH2:15][CH2:16][O:17][CH2:18][P:19]([OH:24])([OH:21])=[O:20])=[C:2]([Cl:1])[N:10]=1참가 물질
4
실험 절차
To a solution of 6-chloro-9-[2-(diethoxyphosphorylmethoxy)ethoxy]-2-formamidopurine (0.370 g, 0.91 mmol) in dry dimethylformamide (5 ml) was added trimethylsilyl bromide (1.3 ml, 9.6 mmol) and the solution stirred at ambient temperature for 3 hours. The solvent was removed under reduced pressure and the residue co-evaporated with acetone:water 1:1 (×2). The solid residue obtained was crystallised from hot water to give the title compound as a tan solid (0.15 g, 51%), m.p. 190°-195° C. IR: νmax (KBr) 3480, 3430, 3200, 3150, 2920, 1660, 1625, 1570, 1525, 1480, 1370, 1320, 1235, 1195, 1125, 1105, 1030, 995, 950, 920, 880, 780 cm-1. 1H NMR: δH [(CD3)2SO] 3.63 (2H, d, J=8.52 Hz, OCH2P), 3.81 (2H, m, CH2OCH2P), 4.45 (2H, m, N-OCH2), 2.75-5.25 (2H, broad, D2O exchangeable PO(OH)2), 7.11 (2H, br.s, D2O exchangeable NH2), 8.37 (1H, s, H-8). Found: C,28.89; H,3.51; N,21.15%. C8H11N5O5PCl. 0.5H2O requires: C,28.88; H,3.63; N,21.06%.