Potassium Cyanide → HCID 66802722, compound

Participants

Reaction Steps

4-Chloro-6-(2,3-dihydro-indol-1-yl)-[1,3,5]triazin-2-ylamine (Intermediate 40, 680 mg, 2.48 mmol), potassium cyanide (323 mg, 4.96 mmol) and 18-crown-6 (328 mg, 1.24 mmol) were charged to a round-bottomed flask then taken up in DMF (12 mL). The resulting mixture was lowered into a heating block preheated to 110 C and stirred under nitrogen for 2 h and then at room temperature for 56 h. The reaction was then diluted with EtOAc (60 ml) and extracted with 5% aq. sodium carbonate solution (2×10 ml), brine (10 ml) and dried further over anhydrous magnesium sulfate. After evaporation of the solvent the crude residue was purified by FCC over silica gel eluting with heptane:EtOAc 1:0 to 8:2 to 1:1 to 0:1 and the column flushed with THF to give the title compound (155 mg, 26%). Method B HPLC-MS: MH+ requires m/z=239. Found: m/z=239, Rt=1.36 min (75%).

Provenance & Evidence