Triethylamine → 4-(4-Methanesulfonyl-phenoxy)-1-[1-(5-methyl-isoxazol-3-ylmethyl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine

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Reaction Steps

4-(4-Methanesulfonyl-phenoxy)-1-[1-(5-methyl-isoxazol-3-ylmethyl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidine was prepared according to General Procedure H by the reaction of 4-(4-methanesulfonyl-phenoxy)-1-piperidin-4-yl-1H-pyrazolo[3,4-d]pyrimidine trifluoroacetate salt (Intermediate 27) with 5-methylisoxazole-3-carboxaldehyde (available from Aldrich Chemical Company, Inc., Milwaukee, Wis., USA), triethylamine, and sodium triacetoxyborohydride in 1,2-dichloroethane. 1H NMR (400 MHz, DMSO-d6) δ 1.92-1.95 (m, 2H), 2.17-2.33 (m, 4H), 2.40 (s, 2H), 2.95-2.97 (m, 2H), 3.30 (methyl sulfonyl and water peak), 3.57 (s, 2H), 4.74-4.80 (m, 1H), 6.24 (s, 1H), 7.62-7.64 (m, 2H), 8.04-8.07 (m, 2H), 8.37 (s, 1H), 8.55 (s, 1H). Mass spectrum MH+=469.

Provenance & Evidence