Diisobutylaluminumhydride → 2-[4-Chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-yl]ethanol

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Reaction Steps

Ethyl 2-[4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-yl]acetate (9.98 g, 0.285 mol) was dissolved in dry THF (100 mL) under nitrogen. To this was added diisobutyl aluminium hydride (1 M in THF, 95 mL). The reaction was stirred at room temperature for 5.5 hrs before being quenched by careful addition to a saturated solution of Rochelle's salt. The mixture was stirred for 1 hr then allowed to stand overnight. The mixture was extracted with DCM (3×700 mL), the extracts were then combined, dried and concentrated in vacuo. The residue was purified by silica column chromatography eluting with DCM, then 3:1 v/v DCM/ethyl Acetate. Fractions were analysed by TLC, combined and concentrated to give 2-[4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-yl]ethanol as a brown solid (4 g). LCMS RT=4.25 min, M+1=309.

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