Piperidine → HCID 178430017, compound

Participants

Reaction Conditions

Reaction Steps

Using the method described in Example 30 by employing [(1-(3,4-dichlorophenyl)prop-1-enyl]pyrrolidine (freshly prepared before use from 3′,4′-dichloropropiophenone (Aldrich Chemical Company), pyrrolidine and TiCl4 (1.64 g, 6.40 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.30 g, 6.40 mmol), N,N-diisopropylethylamine (1.1 mL, 6.40 mmol), piperidine (1.0 mL, 10.2 mmol), NEt3 (1.1 mL) and SnCl2 (19 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 16 h then the heating was discontinued and the mixture was allowed to cool to room temperature. The residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant to give 511 mg (21%) of 6-(3,4-dichlorophenyl)-2,7-dimethyl-4-piperidylpyrrolo[3,2-d]pyrimidine as a brown colored oil. This compound (511 mg, 1.38 mmol) was dissolved in 5:1 EtOAc/MeOH (30 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (1.40 mL, 1.40 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 90 mg (3%) of the title compound as beige colored needles. Mp: >280° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.64 (br s, 6), 2.27 (s, 3), 2.56 (s, 3), 3.98 (br t, 4, J=5.4), 7.60 (dd, 1, J=2.0, 8.4), 7.78 (d, 1, J=8.4), 7.91 (d, 1, J=2.0), 11.93 (s, 1), 13.97 (s, 1). MS m/z: 375 (M+1 for free base). Anal. Calcd for C19H20Cl2N4.HCl.0.5H2O: C, 54.23; H, 5.27; N, 13.32; Cl, 25.28. Found: C, 54.35; H, 5.23; N, 13.29; Cl, 25.54.

Provenance & Evidence