N-Hydroxyphthalimide → Phthalimide

Participants

Reaction Steps

5-(Benzyloxy)-2-(hydroxymethyl)-4(1H)-pyrimidinone (0.696 g) (3 mmol), 0.787 g (3 mmol) of triphenylphosphine and 0.489 g (3 mmol) of N-hydroxyphthalimide are dissolved in 50 ml of dimethylacetamide. A solution of 0.640 g (3.3 mmol) of diethyl azodicarboxylate in 2 ml of dimethylacetamide is added dropwise at 20° C. The mixture is stirred at room temperature for 20 hours, the solvent is evaporated in a high vacuum and the residual yellow oil is crystallized from ethanol/ether. After recrystallization from ethanol there is obtained N-[(5-benzyloxy)-1,4-dihydro-4-oxo-2-pyrimidinyl]methoxy]phthalimide as white crystals of m.p. 157° C.

Provenance & Evidence