Diisobutylaluminum hydride → (4-Chloroquinazolin-6-yl)methanol

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To a solution of methyl-4-chloroquinazoline-6-carboxylate (3.5 g, 0.015 mol) in dry THF (35 mL) at −25° C. was added DIBAL-H (4.4 g, 0.031 mol) and stirred at −25° C. to RT for 2 h. The reaction mixture was cooled to −10° C. and quenched with 10% aqueous NaHCO3 (9 mL). The reaction mixture was extracted with ethylacetate (100 mL), washed with water, brine and dried. The solvent was removed under vacuum to give 4-chloroquinazoline-6-yl methanol (2 g, 66%).

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