N-(4-Aminophenyl)-N-methylacetamide → HCID 178474550, compound

Participants

Reaction Conditions

Reaction Steps

A 5 L, 4-neck, round-bottomed flask fitted with a mechanical stirrer, digital thermometer, heating and cooling capabilities, condenser, addition funnel, and nitrogen inlet and outlet, was flushed with nitrogen and charged with 479.8 g (2.15 moles) of 2-chloro-N-cyclobutyl-9H-purin-6-amine, 387.5 g (2.36 moles) of N-(4-aminophenyl)-N-methyl-acetamide, and 3.6 L of dry 1-butanol. The mixture was stirred and 2.72 mL (0.02 moles) of chlorotrimethylsilane was added at 25° C. The mixture was heated to 117° C. over about 50 minutes. The reaction temperature and stirring was maintained for 12.5 hours. The mixture was cooled to 50° C. over a period of 2 hours. A temperature of 50° C. was maintained for an additional hour. The product was filtered and the filter cake was washed three times with a total of 1.2 L of 1-butanol. The filter cake was collected and dried at 50° C./20 mm Hg for 24 hours to give 514.3 g of light yellow crystalline solid. Theoretical yield was 832.0 g. Actual yield was 61.8%.

Provenance & Evidence