Pyridine → Acridine

Participants

Reaction Conditions

Reaction Steps

To a cold, stirring methylene chloride solution (30 ml; 0° C.) of 2-chloro-4H-1,2,3-benzodioxaphosphorin-4-one (2.4 ml of 1M methylene chloride solution; 2.4 mmol) and pyridine (0.2 g; 2.4 mmol) was added the DMT-protected pseudonucleoside of Example 2, paragraph A (0.55 g; 0.8 mmol). After stirring at 0° C. for 1 hour, the reaction mixture was poured into 1M TEAB aqueous solution (60 ml). The organic solution was separated, dried, concentrated. The residue was purified by flash column chromatography, eluted with 1% Et3N/CH2Cl2, 1% Et3N/1%CH3OH/CH2Cl2. The combined fraction of the product was washed with 1M TEAB aqueous solution, dried over Na2SO4, and concentrated, affording 0.19 g, 65% of the phosphorylated DMT-protected acridine pseudonucleotide.

Provenance & Evidence