Reaction Steps
Using the method described in Example 30 by employing 2-(1-pyrrolidinylvinyl)benzo[b]furan (freshly prepared before use) (2.21 g, 10.4 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (2.10 g, 10.4 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (1.8 mL, 10.4 mmol), piperidine (Aldrich Chemical Company) (1.6 mL, 16.6 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (31 mL of a 2M solution in DMF). The residue was purified by flash chromatography on silica gel with 95:5 CHCL3:MeOH as elutant to give 560 mg (16%) of the free base as a beige colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.67 (s, 6), 2.44 (s, 3), 3.30 (s, 2, under H20), 3.74 (s, 2), 6.83 (m, 1), 7.28 (br s, 3), 8.77 (br s, 2), 11.36 (s, 1). MS m/z: 333 (M+1). To a hot solution of 2-(2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)benzo[b]furan (Example 85(a)) (0.56 g, 1.69 mmol) in 5:1 EtOAc: MeOH (30 mL) was added 1M etheral HCl (Aldrich Chemical Company) (1.70 mL, 1.69 mmol). Upon cooling crystalliztion occurred and the solid was collected by filtration. This material was washed with Et2O (2×10 mL) and dried under vacuum to give 588 mg (95%) of the title compound as a beige colored solid. Mp: >280° C. 1H NMR (DMSO-d6; 400 MHz) δ 1.73 (s, 6), 2.58 (s, 3), 4.08 (s, 4), 7.00 (s, 1), 7.35 (t, 1, J=7.5), 7.44 (t, 1, J=8.0), 7.71 (d, 1, J=8.2), 7.79 (d, 1, J=7.7), 7.88 (s, 1), 12.48 (s, 1), 14.40 (s, 1). MS m/z: 333 (M+1). Anal. Calcd for C20H20N4O.HCl.H2O: C, 62.25; H, 5.71; N, 14.52; Cl, 9.19. Found C, 62.22; H, 5.94; N, 14.54; Cl, 9.22.
