Diisopropylethylamine → 2-Methoxy-N-(6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-yl)acetamide

To a suspension of 6-(4-nitronaphthalen-1-yloxy)pyrimidin-4-amine (350 mg, 1.24 mmol) in DCM (10.0 mL) and DIPEA (433 μL, 2.48 mmol) at 0° C. was added 2-methoxyacetyl chloride (170 μL, 1.860 mmol). The mixture was warmed to RT and after 3 hr the reaction was quenched by the addition of a solution of NH3 in MeOH (7M, 20 mL) and after a further 10 min was evaporated in vacuo. The residue was partitioned between DCM (30 mL) and saturated aq NaHCO3 solution (30 mL) and the organic layer was separated and washed with brine (30 mL) and then dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, MeOH in DCM, 0-100%, gradient elution) to furnish the title compound as a yellow solid (400 mg, 86%); Rt 4.60 min (Method 1 basic); m/z 355 (M+H)+ (ES+).