Sodium Cyanide → 4-(Benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile

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Reaction Conditions

Reaction Steps

To a stirred solution of N-benzyl-2-chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.500 g, 1.49 mmol) dissolved in DMF (5 mL) was added sodium cyanide (0.366 g, 7.47 mmol). The reaction mixture was heated to 100° C. for 24 h and cooled. Reaction was quenched by adding ice cold water (100 mL) and was extracted with EtOAc (50×3 mL). The organic layer was separated and dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 24 g, 10% EtOAc/hexanes) to afford 4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile (0.200 g, 41.2%). LCMS Condition B-45: retention time 2.95 min, [M−1]=324.2. HPLC Condition B-2: retention time 25.49 min, Purity 98.76%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.68 (s, 2H), 6.92-6.96 (m, 2H), 7.26 (m, 10H), 7.86 (d, J=2.8 Hz, 1H).

Provenance & Evidence