Trichloroisocyanuric Acid → 5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

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Reaction Steps

5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-(4-hydroxymethyl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (90.0 mg, 0.181 mmol) is dissolved in 10 mL of CH2Cl2. Trichloroisocyanuric acid (42.0 mg, 0.181 mmol) and TEMPO (1 mg) are added sequentially to the reaction mixture. The reaction mixture is allowed to stir for 30 min and the organic layer is washed with sodium bicarbonate and water, thus resulting in pure aldehyde. A portion of the aldehyde (40.0 mg, 0.0807 mmol) is dissolved in 2 mL of dry methanol. 200 μL of acetic acid and 100 μL of N-methylpiperazine are added to the reaction mixture and the mixture is allowed to stir for 10 min at room temp. Sodium cyanoborohydride (15 mg, 0.238 mmol) is added and the reaction mixture is stirred for 10 min and then quenched with ammonium hydroxide. The crude material is purified by column chromatography. 1H NMR (CDCl3, 400 MHz) δ 8.34(s, 1H), 8.06 (d, 2H), 7.44 (m, 2H), 7.34-7.28 (m, 3H), 7.18 (m, 2H), 7.03 (m, 1H), 5.31 (s, 2H), 3.66 (m, 2H), 2.89 (m, 6H), 2.71 (s, 3H). HPLC-MS calculated for C29H25Cl3N6O (M+H+) 579.1. Found: 579.1.

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