Diisopropylethylamine → 4-{5-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carbonyl}-piperazine-1-carboxylic acid tert-butyl ester

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Reaction Steps

To a solution of 5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carboxylic acid 5 (0.12 mmol) in DMF (0.5 mL) is added HATU (0.13 mmol) and DIEA (0.36 mmol) at rt. The resulting mixture is stirred for 2 min and then a solution of piperazine-1-carboxylic acid tert-butyl ester (0.12 mmol) in DMF (1 mL) is added. The reaction mixture is stirred at rt for 4 h and directly purified by preparative LCMS to give 4-{5-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-pyridine-2-carbonyl}-piperazine-1-carboxylic acid tert-butyl ester 6 as a white solid. 1H NMR (400 MHz, d6-DMSO) δ 10.32 (s, 1H), 8.89 (s, 2H), 8.39-8.37 (m., 2H), 7.86 (dd, J=4.0 and 8.0 Hz, 1H), 7.71-7.69 (m, 2H), 7.08-7.06 (m, 2H), 3.81 (s, 3H), 3.55-3.51 (bm, 4H), 3.96-3.94 (bs, 4H), 1.42 (s, 9H). MS (m/z) (M+1)+: 491.1.

Provenance & Evidence