Ethylorthoformate → HCID 86705751, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-((((3aR,4S,6R,6aS)-6-((5-amino-6-chloropyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(methyl)amino)propyl)isoindoline-1,3-dione (180 mg, 0.35 mmol) in ethyl orthoformate (5.8 mL, 35 mmol) was treated with acetic acid (4 drops) and heated at 130° C. for 7 hours. The reaction was cooled to room temperature and stirring was continued overnight. The reaction was concentrated and purified by flash chromatography (7N NH3 in MeOH/DMC 4:96) to yield 2-(3-((((3aR,4S,6R,6aS)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl)(methyl)amino)propyl)isoindoline-1,3-dione (165 mg, 90%) as a thick light brown syrup. MS (ESI+) for C26H29ClN6O4 m/z 525.4 [M+H]+.

Provenance & Evidence