Isopropyl iodide → HCID 20434880, compound

Participants

Reaction Steps

A stirred solution of 1-(6,7-dimethoxyquinazolin-4-yl)-4-[(1,1-dioxotetrahydro-1,2,6-thiadiazin-2-yl)methyl]piperidine 1/2 CH3CH2OCOCH3 (0.7 g) (prepared as in Example 9) in dimethylformamide (4.0 cm3) was treated at room temperature with sodium hydride (100 mg. of a 50% dispersion in oil) and the mixture was stirred for 45 minutes. Isopropyl iodide (255 mg) was then added and the resulting mixture was stirred for 6 hours. The solvent was removed in vacuo and the residue was taken into chloroform (50 cm3) and water (25 cm3). The aqueous phase was extracted with chloroform (2×20 cm3) and the dried (MgSO4) extracts were evaporated to yield an oil which was chromatographed on silica (Merck 60.9385) eluting with chloroform to give a gum. Crystallisation from ethyl acetate afforded 1-(6,7-dimethoxyquinazolin-4-yl)-4-([1,1-dioxo-6-isopropyltetrahydro-1,2,6-thiadiazin-2-yl]methyl)piperidine, m.p. 158°-161° (460 mg).

Provenance & Evidence