Methyl iodide → HCID 131734403, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (20 mg, 0.04 mmol) in dry DMF (1 ml) at 0° C. was added sodium hydride (2 mg, 0.05 mmol) and methyl iodide (5 μl, 0.05 mmol) under nitrogen. The resulting mixture was stirred for 30 minutes at 0° C. A saturated solution of NH4Cl was added and the mixture was extracted with DCM (3×10 ml). The combined organic phases were dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 20% EtOAc in cyclohexane) to give the title compound (8 mg, 44%). 1H NMR (500 MHz, CDCl3): 7.39-7.19 (9H, m), 6.85 (1H, s), 4.51-4.50 (2H, d), 3.45-3.43 (2H, d), 2.80-2.70 (2H, m), 2.61-2.51 (4H, m), 2.01-1.88 (1H, m), 2.00 (3H, s), 1.40-1.10 (9H, br).

Provenance & Evidence