N-Hydroxyphthalimide → N-[[5-(benzyloxy)-3,4-dihydro-3-methyl-4-oxo-2-pyrimidinyl]methoxy]phthalimide

Participants

Reaction Conditions

Reaction Steps

Diethyl azodicarboxylate (4.8 g) (20 mmol) are added dropwise at 0° C. while stirring to a mixture of 3.69 g (15 mmol) of 5-(benzyloxy)-2-(hydroxymethyl)-3-methyl-4(3H)-pyrimidinone, 3.26 g (20 mmol) of N-hydroxyphthalimide and 5.24 g (20 mmol) of triphenylphosphine in 100 ml of absolute dimethylacetamide. The mixture is stirred at 0° C. for 2 hours and at room temperature for 16 hours. Subsequently, the solvent is removed in a high vacuum at room temperature. The residue is crystallized from ethanol/diethyl ether. After drying in a high vacuum for 18 hours at room temperature there are obtained 5.5 g of N-[[5-(benzyloxy)-3,4-dihydro-3-methyl-4-oxo-2-pyrimidinyl]methoxy]phthalimide as white crystals of m.p. 170° C.

Provenance & Evidence