N,N,N',N'-Tetramethylmethanediamine → HCID 19042906, compound

Participants

Reaction Steps

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.854 g, 1.14 mL, 8.36 mmol) in CH2Cl2 (10 mL) with acetyl chloride (0.657 g, 0.59 mL, 8.36 mmol) followed by a solution of 5-(pyrimidin-2-yloxy)indole (1.268 g, 6.00 mmol) in CH2Cl2 (110 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(pyrimidin-2-yloxy)indole as a yellow solid. This was treated with finely ground potassium cyanide (1.37 g, 21 mmol) and methyl iodide (2.94 g, 1.28 mL, 21 mmol) in DMF (70 mL) for 16 hr, and after appropriate work-up, 3-cyanomethyl-5-(pyrimidin-2-yloxy)indole was obtained as a light yellow solid, 0.98 g (65%).

Provenance & Evidence