Methyl 2-(Methylthio)pyrimidine-5-carboxylate → (2-(Methylsulfanyl)pyrimidin-5-yl)methanol

Temperature

-78 °C

To a solution of methyl 2-(methylsulfanyl)pyrimidine-5-carboxylate (N1) (023 g, 1.2 mmol) in 20 mL THF at −78° C. was added diisobutylaluminum hydride (3.2 mL, 1.0 M solution in toluene). The reaction mixture stirred for 40 min at −78° C., and then additional diisobutylaluminum hydride (5 eq.) was added dropwise. The reaction mixture was stirred for 2 h, and then quenched with concentrated acetic acid. The reaction mixture was warmed to room temperature and filtered to obtain a biphasic solution. The layers were separated, and the organics were dried over sodium sulfate, filtered, and concentrated to afford [2-(methylsulfanyl)pyrimidin-5-yl]methanol (N2) that gave a mass ion (ES+) of 157.1 for M+H+.

1. stirringThe reaction mixture was stirred for 2 h
2. customquenched with concentrated acetic acid
3. temperatureThe reaction mixture was warmed to room temperature
4. filtrationfiltered
5. customto obtain a biphasic solution
6. customThe layers were separated
7. dry with materialthe organics were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-6bc0b31bddfd465fa02ef70a55890429

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199939B2