6-Methoxy-3-pyridinylamine → N-(6-Methoxypyridin-3-YL)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-YL)-9H-purin-6-YL)quinolin-2-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 5-amino-2-methoxypyridine (50 mg, 0.41 mmol, Aldrich, St. Louis, Mo.) and 2-chloro-3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)quinoline (77 mg, 0.20 mmol) in dioxane (4 mL) at 0° C. was treated with LiHMDS (1 M in THF, 0.51 mL, 0.51 mmol). The reaction mixture was stirred at 0° C. for 1 h and 18 h at room temperature. Then an additional amount of LiHMDS (1 M in THF, 0.51 mL, 0.51 mmol) was added and the reaction mixture stirred at room temperature for 2 h. The reaction was quenched by the addition of MeOH (2 mL) and the solvents were removed under vacuum. Purification of the crude reaction mixture by silica gel chromatography (2 to 3% MeOH/CH2Cl2) provided the title compound as a dark orange solid. m/z (ESI, +ve ion) 468 (M+H)+.

Provenance & Evidence