2-Methoxy-N-(6-(4-nitrophenoxy)pyrimidin-4-yl)acetamide → N-(6-(4-Aminophenoxy)pyrimidin-4-yl)-2-methoxyacetamide

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Reaction Steps

A solution of 2-methoxy-N-(6-(4-nitrophenoxy)pyrimidin-4-yl)acetamide (730 mg, 2.53 mmol) in a mixture of MeOH and DCM (1:1 v/v, 80 mL) containing AcOH (5 drops) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, RT, 10% Pt/C, full hydrogen mode) and was then evaporated in vacuo. The residue was partitioned between DCM (100 mL) and saturated aq NaHCO3 solution (25 mL). The organic layer was separated and washed with brine (25 mL) and then dried (MgSO4). Evaporation of the volatiles in vacuo gave the title compound, Intermediate N1, (560 mg, 66%, estimated 82% purity); Rt 0.93 min (Method 2); m/z 275 (M+H)+ (ES+). This material was used directly in the next step without further purification.

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