Reserpine → tert-Butyl 4-[7-amino-1-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidine-3-yl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate

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Reaction Steps

The title compound was prepared from 3-iodo-1-(4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-7-amine and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydro-1-pyridinecarboxylate in the manner described for the preparation of tert-butyl 4-[7-amino-1-(3-methoxy-4-nitrophenyl)-1H-pyrazolo[4,3-d]pyrimidin-3-yl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate: 1H NMR (DMSO-d6, 400 MHz) δ 8.44 (m, 3H), 7.76 (d, 2H), 7.53 (m, 1H), 7.05 (bs, 2H), 4.13 (m, 2H), 3.58 (m, 2H), 2.67 (m, 2H), 1.44 (s, 9H); RP-HPLC (Hypersil HS C18, 5 μm, 100 A, 250×4.6 mm; 5%-100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 21.70 min; MS: MH+ 438.1, M−H+ 436.1

Provenance & Evidence