Diisobutylaluminum hydride → (2-(Methylsulfanyl)pyrimidin-5-yl)methanol

Temperature

-70 °C

To a cold suspension of methyl 2-(methylthio)pyrimidine-5-carboxylate (1.74 g, 9.4 mmol) in dichloromethane (20 mL, −70° C.) was added DIBAL (20.8 mL, 20 mmol) dropwise via an addition funnel. The mixture was stirred under nitrogen at −70° C. for 1 hour and then at −50° C. for 3 hours. The reaction was diluted with dichloromethane (50 mL) and quenched with a suspension of sodium sulfate decahydrate (10 g) in water (50 mL). The slurry was filtered through celite and the filtrate was concentrated. The residue was purified by flash chromatography (silica gel) using 100% ethyl acetate to afford the desired compound (0.7813 g, 39%) as a yellow solid. 1H-NMR ((CD3OD, 400 MHz) δ 8.53 (s, 2H), 4.56 (s, 2H), 2.54 (s, 3H); ES-HRMS m/z 157.0409 (M+H C6H8N2OS requires 157.0430).

1. waitat −50° C. for 3 hours
2. customquenched with a suspension of sodium sulfate decahydrate (10 g) in water (50 mL)
3. filtrationThe slurry was filtered through celite
4. concentrationthe filtrate was concentrated
5. customThe residue was purified by flash chromatography (silica gel)

ORD record

ord-ea6ce4cc348a444f94d69b94b2f0059c

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629363B2