Piperidine → HCID 178423325, compound

Participants

Reaction Conditions

Reaction Steps

Using the method described in Example 30 by employing [2-(4-fluorophenyl)-1-methylvinyl]pyrrolidine (freshly prepared before use from (4-fluorophenyl) acetone (Aldrich Chemical Company), pyrrolidine and TiCl4 (1.64 g, 8.00 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.66 g, 8.00 mmol), N,N-diisopropylethylamine (1.4 mL, 8.00 mmol), piperidine (1.3 mL, 12.8 mmol), NEt3 (1.8 mL) and SnCl2 (24 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 50:50 EtOAc/hexanes as eluant to give 108 g (4%) of 6-[(4-fluorophenyl)methyl]-2-methyl-4-piperidylpyrrolo[3,2-d]pyrimidine as a white colored solid and 172 mg (7%) of 7-(4-fluorophenyl)-2,6-dimethyl-4-piperidylpyrrolo[3,2-d]pyrimidine as a white colored solid.

Provenance & Evidence