Adenine → HCID 21765788, compound

Participants

Reaction Steps

To a flame-dried argon blanketed round bottom flask equipped with a magnetic stir bar and condenser was added adenine (2.14 g, 15.8 mmole), K2CO3 (4.37 g, 31.6 mmole), 18-crown-6 (417 mg, 1.58 mmole) and DMF (400 mL). This mixture was allowed to stir at room temperature for 30 minutes under a stream of argon. A solution of (3S-trans)-tetrahydro-5-(dimethoxymethyl)-3-furanol-4-methylbenzenesulfonate. Compound IV(e), (5.0 g, 15.8 mmole) in 100 mL DMF was then added dropwise to the stirring mixture; the resultant mixture was warmed to 80° C., and stirred at that temperature overnight. Filtration, followed by evaporation of DMF, afforded a solid residue. This material was passed through a silica gel pad using a 7% MeOH/93% CH2Cl2 solution as eluant. Fractions containing the desired product were collected and evaporated to yield 3.0 g (71%) of Compound VI as a white solid:

Provenance & Evidence