HCID 7749283, compound → HCID 44239508, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (30% in H2O; 153 μL, 1.50 mmol) was added dropwise to a stirred solution of 4,6,7-trimethoxyquinazoline 1i (110 mg, 0.5 mmol), concentrated H2SO4 (54 μL, 1.0 mmol), 3-iodooxetane (183 mg, 1.0 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) in DMSO (5 mL) at 60 °C. After 1-2 min a further portion of iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) was added and the mixture was stirred at 60 °C for 30 min. Further H2O2 (153 μL, 1.5 mmol) and iron(II) sulfate heptahydrate (42 mg, 0.15 mmol) was added, and the mixture was stirred at 60 °C for a further 60 min. Ater allowing to cool, the mixture was poured into a 0.2 M solution of NaOH (50 mL) and Et2O (30 mL). The aqueous and organic layers were partitioned and the aqueous layer was saturated with solid NaCl, then extracted with Et2O (2 x 25 mL). The combined organic - 9 -extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude oil. The oil was purified by preparative thin-layer chromatography to give a mixture of recovered 4,6,7-trimethoxyquinazoline 1i and product, followed by desired product 2i (64 mg, ca. 83% pure, 38% yield adjusted for purity). An analytical sample of the product 2i (83% purity) was purified further by perparative high-performance liquid chromatography to give material for data purposes (column: Gemini C6P (phenyl hexyl); size: 100 x 21.2 mm; particle size: 5 μM; eluent: 3-70% CH3CN in 10 mM aqueous Et2NH; run time: 20 min; detection: UV at 254 nM; retention time: 7.76 min)

Provenance & Evidence