Hexamethyldisilazane → HCID 131727138, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of of benzoic acid 4-acetoxy-[1,3]dioxolan-2(R)-ylmethyl ester (6.02 g, 18.8 mm) in dichloroethane (56 mL) was charged TMSI (3.2 mL) at −15° C. After the addition the reaction was stirred for 2 hours at −15° C. HMDS (5.9 mL, 28.2 mm) was added followed by 2-amino-6-cyclopropylaminopurine (3.57 g, 18.8 mm). The reaction was allowed to warm up to room temperature and was stirred for 48 hours followed by 3 hours of reflux. The reaction was cooled to room temperature and poured into saturated sodium bicarbonate solution. The mixture was filtered through a pad of Celite and the organic layer was separated. The aqueous layer was back-extracted with dichloromethane (2×20 mL). The combined organic phases were dried over sodium sulfate and concentrated to a residue. The crude product was purified by flash chromatography (40/60:EtOAc/Hexane followed by DCM/MeOH:25/1) to produce benzoic acid 4(R,S)-(2-amino-6-cyclopropylamino-purin-9-yl)-[1,3]dioxolan-2(R)-ylmethyl ester benzoate-cyclopropylaminopurine (2.25 g, 27% yield, cis/trans:1/1.25).

Provenance & Evidence