Hydrochloric Acid → HCID 178430024, compound

Participants

Reaction Steps

Using the method described in Example 30 by employing (1-phenylbut-1-enyl)pyrrolidine (freshly prepared before use) (2.10 g, 11.3 mmol), 4,6-dichloro-5-nitropyrimidine (Aldrich Chemical Company) (2.18 g, 11.3 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (2.0 mL, 11.3 mmol), piperidine (1.8 mL, 18.1 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (Aldrich Chemical Company) (34 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 407 mg (12%) of the product as a faint yellow colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.64 (br s, 6), 2.30 (s, 3), 3.72 (br s, 4), 7.44 (t, 1, J=7.3), 7.53 (t, 2, J=7.53), 7.66 (d, 2, J=7.3), 8.29 (s, 1), 10.95 (s, 1). MS m/z: 293 (M+1). To a solution of 7-methyl-6-phenyl-4-piperidylpyrrolo[3,2-d]pyrimidine (0.22 g, 0.76 mmol) in 5:1 EtOAc: MeOH (30 mL) was added 1M etheral HCl (Aldrich Chemical Company) (760 mL, 0.73 mmol). The precipitate was collected by filtration, washed with ether (3×15 mL) and dried under vacuum to give 224 mg (90%) of the title compound as a white colored solid. Mp: 281-282.5° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.71 (br s, 6), 2.32 (s, 3), 4.04 (br s, 4), 7.52-7.61 (m, 3), 7.68 (d, 2, J=7.1), 8.56 (s, 1), 12.05 (s, 1), 14.67 (s, 1). MS m/z: 293 (M+1). Anal. Calcd. for C24H24N4.HCl: C, 65.74; H, 6.44; N, 17.04; Cl, 10.78. Found C, 65.64; H, 6.51; N, 17.04; Cl, 10.71.

Provenance & Evidence