Ethylorthoformate → HCID 86705762, compound

Participants

Reaction Steps

A solution of 2-(3-((((3aR,4R,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 (0.22 g, 0.39 mmol) in ethyl orthoformate (2.3 mL, 14 mmol) was treated with acetic acid (8 drops) and heated at reflux for 3.25 h; HPLC indicated nearly complete consumption of starting material. The reaction mixture was cooled to rt, diluted with toluene (10 mL), and concentrated in vacuo to remove most of the volatiles, and further concentrated under the flow of air. The resulting clear, dark brown oil was purified by column chromatography (2×22 cm silica; 0-1% 7 N NH3 in CH3OH/CH2Cl2) to afford the title compound (0.19 g, 85%) as a pale yellow foam: MS (ESI+) for C26H29ClN6O4 m/z 525.2 [M+H]+; HPLC purity 92% (ret. time, 2.917 min).

Provenance & Evidence