N,N,N',N'-Tetramethylmethanediamine → HCID 19042922, compound

Participants

Reaction Steps

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (1.18 g, 1.58 mL, 11.5 mmol) in CH2Cl2 (10 mL) with acetyl chloride (0.90 g, 0.81 mL, 11.5 mmol) followed by a solution of 5-(4-methoxypyrimidin-2-yloxy)indole (2.0 g, 8.2 mmol) in CH2Cl2 (100 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(4-methoxypyrimidin-2-yloxy)indole as a white solid. This was treated with finely ground potassium cyanide (1.75 g, 26.8 mmol) and methyl iodide (3.80 g, 1.65 mL, 26.8 mmol) in DMF (130 mL) for 16 hr, and after appropriate work-up, 3-cyanomethyl-5-(4-methoxypyrimidin-2-yloxy)indole was obtained as a white solid, 2.20 g (96%).

Provenance & Evidence