[N:1]([C:4]1[C:5]2[S:25][CH2:24][CH2:23][C:6]=2[N:7]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[N:9]=1)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:8]3[N:9]=[C:4]([NH2:1])[C:5]4[S:25][CH2:24][CH2:23][C:6]=4[N:7]=3)[CH2:15][CH2:14]2)=[CH:21][CH:20]=1
0.820 g (1.76 mmol) of 4-azido-2-[4-(4-chlorophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidine (IV) is placed in 10 mL of tetrahydrofuran and 3.80 mL (3.80 mmol) of lithium aluminum hydride (1M solution in tetrahydrofuran) is slowly added dropwise. The reaction mixture is stirred for 4 hours at ambient temperature. Then 0.55 mL of 1N sodium hydroxide solution and 0.50 mL of water are added, the mixture is boiled for 0.3 hours, then cooled again. It is filtered, the filtrate is dried and evaporated to dryness. The residue is extracted with ethyl acetate and 1 N hydrochloric acid. The product precipitates out, is suction filtered, then extracted with ethyl acetate and 1 N sodium hydroxide solution. The organic phase is washed with water, dried, and evaporated to dryness. The residue is stirred with petroleum ether. 0.513 g of product V (84%) is obtained as a solid (m.p. 176-178° C.). 1H NMR (400 MHz, DMSO): 7.24 (2H, d); 6.98 (2H, d); 6.30 (2H, s); 3.77-3.68 (4H, m); 3.22 (2H, t); 3.17-3.09 (4H, m); 2.99 (2H, t).
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