Acetic Anhydride → 3-(hydroxymethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one acetate

Participants

Reaction Steps

To 3.0 g of 3-(hydroxymethyl)-4H-pyrimido [2,1-a]isoquinolin-4-one (13.3 mmole) suspended in 100 ml chloroform with 10 ml of triethylamine and a trace of 4-dimethylaminopyridine was added 5.0 g of acetic anhydride (50.0 mmole). The reaction mixture was refluxed for 2 hours, then cooled to room temperature and washed twice with water. The organic layer was dried and concentrated in vacuo to give a crude solid which was crystallized from methylene chloride/hexane to yield 3-(hydroxymethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one acetate as yellow crystals (2.09 g, 59% yield) of the formula: ##STR22## having a melting point of 173.3° C. and the following elemental analysis:

Provenance & Evidence