Piperidine → HCID 178423683, compound

Participants

Reaction Steps

Using the method described in Example 30 by employing[1-(3,4-dimethylphenyl)vinyl]pyrrolidine (freshly prepared before use from 3,4-dimethyl acetophenone (Aldrich Chemical Company), pyrrolidine and TiCl4 (1.22 g, 6.07 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.30 g, 6.07 mmol), N,N-diisopropylethylamine (1.1 mL, 6.07 mmol), piperidine (1.0 mL, 9.7 mmol), NEt3 (1.1 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 mpurified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant to give 605 mg (31%) of 6-(3,4-dimethylphenyl)-2-methyl-4-piperidylpyrrolo[3,2-d]pyrimidine as a beige colored solid. This material (605 mg, 1.88 mmol) was dissolved in 5:1 EtOAc/MeOH (35 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (1.90 mL, 1.90 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 518 mg (24%) of the title compound as a beige colored powder. Mp: 198-201° C. 1H NMR (DMSO-D6; 400 MHz): δ 1.70 (br s, 6), 2.30 (s, 3), 2.33 (s, 3), 2.56 (s, 3), 4.05 (s, 4), 6.84 (s, 1), 7.32 (d, 1, J=7.9), 7.70 (d, 1, J=7.8), 7.74 (s, 1), 11.91 (s, 1), 14.38 (s, 1). MS m/z: 321 (M+1 for free base). Anal. Calcd for C20H24N4.HCl.0.75H2O: C, 64.95; H, 7.17; N, 15.15; Cl, 9.47. Found: C, 65.13; H, 7.11; N, 14.98; Cl, 9.54.

Provenance & Evidence