Methyl 5-bromo-2-(methylsulfanyl)pyrimidine-4-carboxylate → (5-Bromo-2-(methylthio)pyrimidin-4-yl)methanol

関与物質

反応手順

To a cold (−10° C.˜0° C.) THF (19.00 mL) solution of methyl 5-bromo-2-(methylthio)pyrimidine-4-carboxylate (Step A, 1 g, 3.80 mmol) was added diisobutylaluminum hydride (1M, 9.50 mL, 9.50 mmol) while internal temperature was below 0° C. An aliquot taken immediately after addition indicated completion of reaction. The crude mixture was quenched with NH4Cl (aq.). Volatiles were removed under reduced pressure. The resulting pot residue was worked up with brine, extracted with EtOAc, dried (Na2SO4), filtered and evaporated to afford a dark mixture. The dark residue was purified by preparative HPLC (Kromasil 100-5C18, 100×21.1 mm) eluting with MeCN/water+0.1% TFA (10% to 80% organic in 10 min, then to 100% in 2 min). Related fractions were pooled and evaporated in vacuo to afford an aqueous mixture. The resulting mixture was extracted with EtOAc and washed with aqueous NaHCO3, dried (Na2SO4), filtered and concentrated to afford a brown oil. After further drying under reduced pressure, this oil solidified to a crystalline solid. LCMS calc.=235.94; found=236.88.

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