Methyl iodide → HCID 68588479, compound

Participants

Reaction Conditions

Reaction Steps

(R)-2-Bromo-N-methyl-N-(tetrahydrofuran-3-yl-[1,2,4]triazolo[1,5-a]pyridin-5-amine. (R)-2-Bromo-N-(tetrahydrofuran-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine (500.0 mg, 1.766 mmol) was suspended in 1,2-dimethoxyethane (8.83 mL) and cooled to 0° C. The reaction was purged with nitrogen followed by the addition of sodium hydride (89.0 mg, 3.53 mmol, 95%). The mixture was allowed to stir for 10 min. Iodomethane (330.0 μL, 5.30 mmol) was added dropwise and the reaction mixture was allowed to warm to room temperature and stir for 16 h. Ethyl acetate was added to the reaction and allowed to stir for 1 min followed by an extraction with ethyl acetate and water. The organics were washed with brine and dried with magnesium sulfate. Organic volatiles were removed under reduced pressure and purified using silica gel chromatography on an Emrys Biotage SP1 (10-100% ethyl acetate in hexanes) over 1.2 L. The desired fractions were combined and organic volatiles removed under reduced pressure to afford (R)-2-bromo-N-methyl-N-(tetrahydrofuran-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-5-amine (373.8 mg, 1.258 mmol, 71.2% yield). MS (ESI) m/z 297.1 [M]+, 299.1 [M+2]+.

Provenance & Evidence