Methyl iodide → HCID 178430022, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of 7-methyl-6-phenyl-4-piperidylpyrrolo[3,2-d]pyrimidine (Example 89) (177.3 mg, 0.61 mmol) in THF (10 mL) under a nitrogen atmosphere was added LiHMDS (1.0 M soln from Aldrich Chemical Company) (1.3 mL, 1.27 mmol). This mixture was stirred at 0° C. for 0.5 h then CH3I (Aldrich Chemical Comapny) (41 mL, 0.67 mmol) was added. The 0° C. bath was removed and the solution stirred at room temperature for 2.5 h. The reaction mixture was poured into a separatory funnel containing EtOAc (35 mL) and H2O (50 mL). The organic solution was collected washed with H2O (3×40 mL), saturated NaCl (70 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified via flash chromatography on silica gel 95:5 CHCl3/MeOH as eluant to give 164 mg (86%) of the title compound as a beige colored solid. Mp: 123.0-125.0° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.68 (m, 2), 1.78 (m, 4), 2.30 (s, 3), 3.42 (br s, 4), 3.66 (s, 3), 7.44-7.54 (m, 5), 8.61 (s, 1). MS m/z: 307 (M+1).

Provenance & Evidence