Diisobutylaluminum hydride → 1-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-one (146 mg, 0.48 mmol) in THF (5 mL) at −78° C. was added DIBAL-H (580 μL, 0.58 mmol, 1M solution in toluene) and the resulting mixture warmed to 0° C. and stirred for 1.5 hours. The reaction mixture was cooled to −78° C. before the addition of further DIBAL-H (480 μL, 0.48 mmol) and the mixture warmed to 0° C. and stirred for 2 hours. The reaction mixture was quenched with Rochelle's salt (1M aqueous solution) and the mixture extracted with ethyl acetate. The combined organic extracts were washed with brine, then dried (Na2SO4) and concentrated in vacuo affording 1-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-ol (148 mg, quantitative). LCMS: RT=2.84 min, [M+H]+=308/310/312.

Provenance & Evidence