Hexamethyldisilazane → HCID 58203538, compound

Participants

Reaction Steps

A mixture of N-(3,5-dimethyl-phenyl)-N-(5-ethyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-acetamide (109) (301 mg, 1 mmol), hexamethyldisilazane (5 mL), and chlorotrimethylsilane (5 drops) was refluxed for 4 hr. After cooling to room temperature, the mixture was evaporated in vacuo. The residue was dissolved in acetonitrile (5 mL). Chloromethyl ethyl ether (110 μL, 1.2 mmol) and SnCl4 (1 M in dichloromethane, 100 μL, 0.1 mmol) were added. The mixture was stirred at room temperature for 16 hrs. Excess sodium bicarbonate was then added and the mixture was stirred for 1 hr. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1)) to afford 162 mg (45%) of a white solid. m.p. 182-183° C.; HRMS (EI) Calcd. 359.184507. Found 359.183174.

Provenance & Evidence