Piperidine → HCID 178423305, compound

Participants

Reaction Conditions

Reaction Steps

Using the method described in Example 30 by employing [1-(2-naphthyl)vinyl]pyrrolidine (freshly prepared before use from 21-acetylnaphthone (Aldrich Chemical Company), pyrrolidine and TiCl4 (1.91 g, 8.60 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.78 g, 8.60 mmol), N,N-diisopropylethylamine (1.5 mL, 8.6 mmol), piperidine (1.4 mL, 13.8 mmol), NEt3 (1.9 mL) and SnCl2 (23 mL of a 2 M soln in DMF). In this example the SnCl2 solution was added to the reaction mixture at 140° C. The mixture was stirred at 140° C. for an additional 2.5 h then the heating was discontinued and the mixture was allowed to cool to room temperature. The mixture was stirred at room temperature an additional 36 h. The residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant to give 1.25 g (55%) of 2-methyl-6-(2-naphthyl)-4-piperidylpyrrolo[3,2-d]pyrimidine as a beige colored solid. This compound (1.25 g, 3.64 mmol) was dissolved in 5:1 EtOAc/MeOH (60 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (3.60 mL, 3.60 mmol). The solution was allowed 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 1.02 g (40%) of the title compound as a yellow colored powder. Mp: >280° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.67 (br s, 6), 2.52 (s, 3), 4.04 (t, 4, J=4.9), 6.98 (s, 1), 7.55 (m, 2), 7.94 (t, 1, J=4.0), 8.00 (d, 1, J=5.4), 8.02 (br s, 2), 8.50 (s, 1), 12.09 (s, 1), 14.27 (s, 1). MS m/z: 343 (M+1 for free base). Anal. Calcd for C22H22N4.HCl.1.5H2O: C, 65.09; H, 6.46; N, 13.81; Cl, 8.73. Found: C, 65.00; H, 66.45; N, 13.80; Cl, 8.76.

Provenance & Evidence