Adenine → Ro 24-5098

Reaction equation

[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.C1OCCOCCOCCOCCOCCOC1.CC1C=CC(S(O[C@@H:40]2[CH2:44][O:43][C@@H:42]([CH2:45][OH:46])[CH2:41]2)(=O)=O)=CC=1>CN(C=O)C>[NH2:10][C:9]1[N:1]=[CH:2][N:3]=[C:4]2[C:8]=1[N:7]=[CH:6][N:5]2[C@H:40]1[CH2:44][O:43][C@@H:42]([CH2:45][OH:46])[CH2:41]1

Participants

Procedure

To a flame-dried argon blanketed round bottom flask equipped with a magnetic stir bar and condenser was added adenine (50 mg, 0.37 mmole) K2CO3 (100 mg, 0.73 mmole), 18-crown-6 (97 mg, 0.37 mmole) and DMF (10 mL). This mixture was allowed to stir at room temperature for 30 minutes under a stream of argon. A solution of (2R-trans)-tetrahydro-4-[[(4-methylphenyl)sulfonyl]oxy]-2-furanmethanol, Compound IV(c), (100 mg, 0.37 mmole) in 2 mL DMF was then added dropwise to the stirring mixture. The resultant mixture was warmed to 80° C., and stirred at that temperature overnight. After removal of the solvent in vacuo, the solid residue was purified by flash chromatorgraphy using a 10% MeOH/90% CH2Cl2 solution as eluant. This isolated material was further purified by reverse-phase HPLC using a gradient elution system of CH3CN/H2O to yield 25 mg (29%) of Compound I as a white solid. An analytical sample was crystallized from methanol: mp 183°-185°, [α]D +47.91 (c 0.67, MeOH).