Ammonium fluoride → 2-(2-Cyclohexylethoxy)-9-pentofuranosyl-9H-purin-6-amine

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Reaction Steps

To a 100-mL one-neck round bottom flask was added under a nitrogen atmosphere 2-[2-(cyclohexyl)ethoxy]-2′,3′,5′-tri-O-(TERT-butyldimethylsilyl)-adenosine (3.3 g, Example 10), anhydrous methanol (50 mL), and ammonium fluoride (1.7 g, 45.8 mmol). The resulting solution was heated to reflux for 24 hours, at which time HPLC indicated the disappearance of starting material. The reaction was cooled to room temperature, concentrated in vacuo on a rotary evaporator, and the resultant solids partitioned between ethyl acetate (50 mL) and water (30 mL). The mixture was stirred for 10 minutes, the layers separated, and the aqueous portion extracted with additional ethyl acetate (50 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to a light yellow solid. The product was purified by passing the oil through a plug of silica gel, eluting with CH2Cl2, 2% methanol in CH2Cl2, 5% methanol in CH2Cl2, and 10% methanol in CH2Cl2. Fractions containing the product were combined and concentrated at reduced pressure to afford the desired product as a white solid. 1.2 g (39%). m.p.: 105–112° C.

Provenance & Evidence