Boron tribromide → HCID 23624294, compound

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Reaction Steps

4-[4-amino-6-(5-chloro-1H,3H-benzo[de]isochromen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-butyramide (100 mg, 0.24 mmol) obtained in Example 339 was dissolved in dichloromethane (4 ml) at room temperature. To the solution was added boron tribromide (1.0M in dichloromethane, 0.96 ml) and the resulted suspension was stirred overnight. The mixture was concentrated followed by dilution with N,N-dimethylformamide (6 ml). To the mixture were added sodium sulfide nonahydrate (220 mg, 2.46 mmol) and N-ethyldiisopropylamine (0.2 ml) successively at room temperature for 6 hours. The mixture was diluted with ethyl acetate (100 ml), and washed with water (50 ml, 3 times), brine successively, and then dried over anhydrous sodium sulfate. After removal of inorganic salts by filtration, the filtrate was concentrated. The resulting residue was purified by silica gel thin layer chromatography (developing solvent; dichloromethane/methanol=9:1) to give 4-[4-amino-6-(5-chloro-1H,3H-2-thia-phenalen-6-yl)-[1,3,5]triazin-2-ylsulfanyl]-butyramide (52 mg, 49%) as a yellow solid.

Provenance & Evidence