Piperidine → HCID 178423278, compound

Participants

Reaction Steps

Using the method described in Example 30 by employing ((1-(2-5,6,7,8-tetrahydronaphthyl)vinyl)pyrrolidine (freshly prepared before use from 6-acetyltetralin (Lancaster Chemical Company), pyrrolidine and TiCl4 (1.37 g, 6.03 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.20 g, 6.03 mmol), N,N-diisopropylethylamine (1.0 mL, 6.03 mmol), piperidine (1.0 mL, 9.6 mmol), NEt3 (1.0 mL) and SnCl2 (18 mL of a 2 M soln in DMF). In this example the reaction mixture was stirred at room temperature for 48 h after the addition of 2 M SnCl2. The residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant to give 692 mg (33%) of 2-methyl-4-piperidyl-6-(2-5,6,7,8-tetrahydronaphthyl)pyrrolo[3,2-d]pyrimidine as a white colored solid. This material (692 mg, 2.00 mmol) was dissolved in 5:1 EtOAc/MeOH (40 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (2.00 mL, 2.00 mmol). The solution was left to cool to room temperature. The resulting crystals were collected by filtration, washed with EtOAc (2×10 mL), Et2O (3×15 mL) and dried under vacuum at 60° C. to give 563 mg (24%) of the title compound as a faint yellow colored solid. Mp: 175-177° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.71 (br s, 6), 1.78 (m, 4), 2.57 (s, 3), 2.82 (d, 4, J=16.0), 4.06 (br s, 4), 6.93 (s, 1), 7.23 (d, 1, J=8.6), 7.65-7.67 (m, 2), 11.92 (s, 1), 14.45 (s, 1). MS m/z: 347 (M+1 for free base). Anal. Calcd for C22H26N4.HCl.2.0H2O: C, 63.02; H, 7.40; N, 13.37; Cl, 15 8.35. Found: C, 63.18; H, 7.43; N, 13.41; Cl, 8.62.

Provenance & Evidence