Piperidine → HCID 178423282, compound

Participants

Reaction Steps

Using the method described in Example 30 by employing [1-(2-chlorophenyl]vinyl]pyrrolidine (freshly prepared before use from 2′-chloro acetophenone (Aldrich Chemical Company), pyrrolidine and TiCl4 (1.06 g, 5.12 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.10 g, 5.12 mmol), N,N-diisopropylethylamine (0.9 mL, 5.12 mmol), piperidine (0.8 mL, 8.2 mmol), NEt3 (0.9 mL) and SnCl2 (15 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 442 mg (25%) of 2-methyl-4-piperidyl-6-(2-chlorophenyl)pyrrolo[3,2-d]pyrimidine as a brown colored solid. This material (450 mg, 1.37 mmol) was dissolved in 5:1 EtOAc/MeOH (35 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (1.40 mL, 1.40 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 343 mg (17%) of the title compound as brown colored needles. Mp: 240-241.5° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.71 (br s, 6), 2.59 (s, 3), 4.03 (s, 4), 6.74 (s, 1), 7.55 (dquintet, 2, J=1.3, 7.8), 7.70 (dt, 2, J=0.9, 8.2), 12.34 (s, 1), 14.64 (s, 1). MS m/z: 327 (M+1 for free base). Anal. Calcd for C18H19ClN4.HCl.H2O: C, 56.70; H, 5.82; N, 14.70; Cl, 18.59. Found: C, 56.93; H, 5.91; N, 14.63; Cl, 18.70.

Provenance & Evidence