Piperidine → HCID 178488896, compound

Participants

Reaction Conditions

Reaction Steps

Using the method described in Example 30 by employing 4-(1-pyrrolidinylprop-1-enyl)-1-methoxy benzene (freshly prepared before use from 4′-methoxy propiophenone (Aldrich Chemical Company), pyrrolidine and TiCl4 (1.77 g, 8.16 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.70 g, 8.20 mmol), N,N-diisopropylethylamine (1.4 mL, 8.20 mmol), piperidine (1.3 mL, 13.1 mmol), NEt3 (1.4 mL) and SnCl2 (25 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 894 mg (33%) of 1-[2,7-dimethyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl]-4-methoxybenzene as a brown colored foam. This compound (440 mg, 1.31 mmol) was dissolved in 5:1 EtOAc/MeOH (20 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (1.30 mL, 1.30 mmol). The solution was allowed to cool to room temperature. The resulting crystals were collected by filtration, washed with EtOAc (2×10 mL), Et2O (3×15mL) and dried under vacuum at 60° C. to give 202 mg (14%) of the title compound as a beige colored sandy solid. Mp: >280° C. 1H HMR (DMSO-d6; 400 MHz): δ 1.62 (br s, 6), 2.24 (s, 3), 2.55 (s, 3), 3.94 (br s, 4), 7.08 (d, 2, J=8.7), 7.55 (d, 2, J=8.7), 11.76 (s, 1), 13.77 (s, 1). MS m/z: 337 (M+1 for free base). Anal. Calcd for C20H24N4O.HCl: C, 64.42/; H, 6.76; N, 15.03; Cl, 9.51. Found: C, 64.40; H, 6.68; N, 15.03; Cl, 9.60.

Provenance & Evidence