Piperidine → HCID 178423285, compound

Participants

Reaction Steps

Using the method described in Example 30 by employing [1-(2,3,4-trichlorophenyl]vinyl]pyrrolidine (freshly prepared before use from 2′,3′,4′-trichloro acetophenone (Aldrich Chemical Company), pyrrolidine and TiCl4 (1.00 g, 3.64 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (0.80 g, 3.64 mmol), N,N-diisopropylethylamine (0.6 mL, 3.64 mmol), piperidine (0.6 mL, 5.80 mmol), NEt3 (0.7 mL) and SnCl2 (11 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 125 mg (9%) of 2-methyl-4-piperidyl-6-(2,3,4-trichlorophenyl)pyrrolo[3,2-d]pyrimidine as a brown colored oil. This material (125 mg, 0.32 mmol) was dissolved in 5:1 EtOAc/MeOH (15 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (0.40 mL, 0.40 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 55 mg (4%) of the title compound as beige colored needles. Mp: 264-266° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.71 (br s, 6), 2.58 (s, 3), 4.03 (s, 4), 6.78 (s, 1), 7.71 (d, 2, J=8.4), 7.88 (d, 2, J=8.5), 12.40 (s, 1), 14.39 (s, 1). MS m/z: 396 (M+1 for free base). Anal. Calcd for C18H17Cl3N4.HCl.1.75H2O: C, 46.59; H, 4.67; N, 12.09; Cl, 30.59. Found: C, 46.64; H, 4.60; N, 11.93; Cl, 30.48.

Provenance & Evidence