4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile synthesis

Yield:916210-08-7 52%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide at 0 - 20; for 2 h;

Steps:

37.A

The title compound from the Preparative Example 20, Step A (549 mg) was dissolved in dry DMF (7 mL) and cooled to 0°C. An excess of NaH and methyl iodide were added subsequently and the mixture was stirred for 2 h while warming to room temperature. The mixture was diluted with EtOAc, washed subsequently with IN aqueous HCl and saturated aqueous NaCl, dried (MgSO₄), filtered, absorbed on silica and purified by chromatography (silica, cyclohexane/EtOAc) to afford the title compound as colorless needles (311 mg, 52%). [MH]⁺ = 189.

References:

WO2006/128184,2006,A2 Location in patent:Page/Page column 163