Piperidine → HCID 178423314, compound

Participants

Reaction Steps

Using the method described in Example 30 by employing [1-(3,5-dichlorophenyl)vinyl]pyrrolidine (freshly prepared before use from 3′,4′-dichloro acetophenone (Aldrich Chemical Company), pyrrolidine and TiCl4 (1.09 g, 4.50 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (0.90 g, 4.50 mmol), N,N-diisopropylethylamine (0.8 mL, 4.50 mmol), piperidine (0.7 mL, 7.2 mmol), NEt3 (0.7 mL) and SnCl2 (14 mL of a 2 M soln in DMF). The residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant to give 86 mg (5%) of 6-(3,4-dichlorophenyl)-2-methyl-4-piperidylpyrrolo[3,2-d]pyrimidine as a tan colored oil. This material (86 mg, 0.24 mmol) was dissolved in 5:1 EtOAc/MeOH (40 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (250 mL, 0.24 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 31 mg (2%) of the title compound as a brown colored solid. Mp: 265-268° C. 1H NMR (DMSO-d6; 500 MHz): δ 1.71 (br s, 6), 2.57 (s, 3), 4.02 (s, 4), 7.06 (s, 1), 7.83 (d, 1, J=8.3), 8.00 (dd, 1, J=1.7, 8.5), 8.34 (d, 1, J=1.7), 12.04 (s, 1), 14.32 (s, 1). MS m/z: 361 (M+1 for free base). Anal. Calcd for C18H18Cl2N4.HCl.H2O: C, 52.00; H, 5.09; N, 13.48; Cl, 25.58. Found: C, 51.65; H, 5.00; N, 13.24; Cl, 25.49.

Provenance & Evidence