2-Nitrophenol → HCID 21277267, compound

Participants

Reaction Steps

(2-Aminopurin-6-yl)trimethylammonium chloride (see Example 1, Step 1; 2.08 g, 9.10 mmol) and o-nitrophenol (2.45 g, 17.63 mmol) were suspended in dry dimethylsulfoxide (25 ml) and triethylamine (5.5 ml) was added. This mixture was stirred at 75° under a refux condenser under N2 for 51/2 hours, then left at room temperature overnight. The reaction mixture was poured into ice-lN HCl (300 ml) and the mixture was extracted with ethyl ether (3×300 ml). The aqueous layer was neutralized by careful addition of solid NaHCO3 and then was extracted with ethyl acetate (3×300 ml). The organic phase was dried over MgSO4, l filtered and evaporated to dryness to give a yellow solid. This material was dissolved in hot ethyl acetate purified by chromatography on silica gel, using ethanol-ethyl acetate (1:9) followed by ethanol-ethyl acetate (15:85) as developing solvents. Chromatographically and spectroscopically pure material was obtained in essentially quantitative yield.

Provenance & Evidence