Diisobutylaluminum hydride → (4-Chloro-2-(methylthio)pyrimidin-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (67 mmol) was dissolved in THF (900 mL) to give a yellow solution. The mixture was cooled in a −78° C. bath under nitrogen atmosphere (internal temp. about −70° C.). DIBAL-H (1 M in THF; 200 mmol) was added over 45 min. via syringe. The reaction was warmed to −60° C. after the addition, and then allowed to warm slowly to 0° C. over night. The reaction was quenched by slow addition of saturated aqueous ammonium chloride (200 mL). The mixture was then warmed to room temperature. Ether (400 mL) and saturated aqueous sodium potassium tartrate (200 mL) were added. The mixture was stirred vigorously for 30 min. After separation of the layers, the aqueous layer was extracted with ether and the combined organics washed with brine, dried with sodium sulfate, filtered and concentrated under vacuum to give (4-chloro-2-(methylthio)pyrimidin-5-yl)methanol as a solid (84%).

Provenance & Evidence