Methylhydrazine → HCID 86629377, compound

To a cloudy solution of 2,4,6-trichloro-pyrimidine-5-carbaldehyde (1.1 g, 5.2 mmol) in chloroform (50 mL) cooled to −78° C. was added in drops methylhydrazine (0.24 g, 5.2 mmol), followed by triethylamine (1.4 mL). The cooling bath was then removed, allowing the mixture to warm to room temperature. The mixture was concentrated to dryness under reduced pressure, and the residue was dissolved in ethanol (50 mL). Triethylamine (1 mL) was added to the mixture, followed by 8-oxa-3-azabicyclo[3.2.1]octane hydrochloride (0.51 g, 3.4 mmol). The mixture was concentrated under reduced pressure and the residue was purified by automated flash chromatography (methanol/chloroform) to provide 3-(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane. MS (ES+): 280.0, 281.9 (M+H)+

1. customThe cooling bath was then removed
2. concentrationThe mixture was concentrated to dryness under reduced pressure
3. dissolutionthe residue was dissolved in ethanol (50 mL)
4. additionTriethylamine (1 mL) was added to the mixture
5. concentrationThe mixture was concentrated under reduced pressure
6. customthe residue was purified by automated flash chromatography (methanol/chloroform)

ORD record

ord-04ab4e5fa5d04a5787fb3f15d237f6ae

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129371B2