Hydrochloric Acid → HCID 178479623, compound

Participants

Reaction Steps

Using the method described in Example 30 by employing 2-(1-pyrrolidinylvinyl) benzo[b]furan (freshly prepared before use) (2.29 g, 10.7 mmol), 4,6-dichloro-5-nitropyrimidine (Aldrich Chemical Company) (2.10 g, 10.7 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (1.9 mL, 10.7 mmol), piperidine (Aldrich Chemical Company) (1.7 mL, 17.1 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (32 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 612 mg (18%) of the free base as a tan colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.68 (s, 6), 3.77 (s, 4), 6.94 (s, 1), 7.32 (d, 2, J=18.9), 7.68 (t, 3, J=26.3), 8.28 (s, 1), 11.54 (s, 1). MS m/z: 319 (M+1). To a hot solution of 2-(4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)benzo[b]furan (0.61 g, 1.92 mmol) in 3:1 EtOAc: MeOH (50 mL) was added 1M etheral HCl (Aldrich Chemical Company) (1.90 mL, 1.92 mmol). Upon cooling crystalliztion occurred and the solid was collected by filtration. Thsi material was washed with Et2O (2×10 mL) and dried under vacuum to give 612 mg (90%) of the title compound as a brown colored solid. Mp: 278.5-281° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.74 (s, 6), 4.10 (s, 4), 7.09 (s, 1), 7.36 (t, 1, J=7.5), 7.45 (t, 1, J=7.9), 7.72 (d, 1, J=8.3), 7.80 (d, 1, J=7.7), 7.93 (s, 1), 8.64 (s, 1), 12.76 (s, 1), 14.66 (s, 1). MS M/z : 319 (M+1). Anal. Calcd for C19H18N4O.HCl.0.5H2O: C, 62.80; H, 5.41; N, 15.42; Cl, 9.76. Found C, 62.89; H, 5.46; N, 15.36; Cl, 9.89.

Provenance & Evidence