Tetrahydrofuran → 2-(2-Chloro-4-morpholino-quinazolin-7-yl)propan-2-ol

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Reaction Conditions

Reaction Steps

To a 25 mL round bottom flask, methyl 2-chloro-4-morpholino-quinazoline-7-carboxylate (0.5 g, 0.001628 mol; prepared as described in Example 7; Scheme 8A) and anhydrous THF were added and cooled to 0° C. To the flask was added methyl magnesium bromide (4.65 ml of 1.4 M in diethyl ether, 0.006514 mol) drop wise at 0° C. and the reaction mixture was stirred at room temperature for 12 h. The reaction mass was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried over anhydrous sodium sulfate and evaporated under reduced to get the crude product. The crude product was purified by column chromatography using 60-120 silica gel and 50% ethyl acetate in hexane to yield the title compound [0.28 g, 56%]. 1H NMR (300 MHz, CDCl3): δ 7.85 (d, J=1.8 Hz, 1H), 7.87 (d, J=8.7 Hz 1H), 7.64 (dd, J′=2.1, J″=8.7 Hz, 1H), 3.87 (s, 8H), 1.63 (s, 6H). LC-MS (ESI): Calculated mass: 307.78; Observed mass: 308.1 (RT: 0.42 min).

Provenance & Evidence