Piperidine → HCID 178489658, compound

Participants

Reaction Conditions

Reaction Steps

Using the method described in Example 30 by employing 1-[2-pyrrolidinylprop-1-enyl]-4-methoxy benzene (freshly prepared before use from 4-methoxy phenylacetone (Aldrich Chemical Company), pyrrolidine and TiCl4 (3.06 g, 14.10 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (2.92 g, 14.10 mmol), N,N-diisopropylethylamine (2.5 mL, 14.10 mmol), piperidine (2.2 mL, 22.6 mmol), NEt3 (3.1 mL) and SnCl2 (42 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 578 g (12%) of 4-methoxy-1-[(2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)methyl]benzene as a brown colored solid and 466 mg (10%) of 1-[2,6-dimethyl-4-piperidylpyrrolo[3,2-d]pyrimidin-7-yl]-4-methoxybenzene as a beige colored solid.

Provenance & Evidence