Methyl iodide → HCID 117667526, compound

Participants

Reaction Conditions

Reaction Steps

6-(5-{[(Tetrahydro-pyran-4-carbonyl)-amino]-methyl}-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (132 mg, 0.29 mmol) is dissolved in DMF (4.0 mL) and cooled down to 0° C. Sodium hydride 60% in mineral oil (14 mg, 0.35 mmol) is added and the mixture is stirred for 10 min. Then iodomethane (0.036 mL, 0.58 mmol) is added and the reaction mixture is warmed up to room temperature for 2 hrs. Saturated NH4Cl aqueous solution (2.0 mL) is added along with water (10 mL) and EtOAc (15 mL). The mixture is stirred for 10 min, the aqueous layer is separated and extracted with EtOAc (2×10 mL). The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 70 mg of 6-(5-{[methyl-(tetrahydro-pyran-4-carbonyl)-amino]-methyl}-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence