1-Ethyl-4-(prop-2-ynyl)piperazine → 4-{5-[3-(4-Methyl-piperazin-1-yl)-prop-1-ynyl]-pyridin-3-yl}-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine

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To a suspension of of 4-(5-bromo-pyridin-3-yl)-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (Example 16) (1 eq, 0.669 mmol, 245 mg) in DME (3.5 ml) are added TEA (2 eq, 1.34 mmol, 135 mg), copper (I) iodide (0.5 eq, 0.335 mmol, 63.7 mg), Pd(PPh3)4 (0.1 eq, 0.067 mmol, 77 mg), and 1-ethyl-4-prop-2-ynyl-piperazine (Tyger Scientific, Ewing, USA) (1 eq, 0.669 mmol, 92 mg). The resulting mixture is heated using microwave radiation for 20 min at 120° C. The mixture is filtered through a pad of Celite and concentrated under reduced pressure. 2M aqueous HCl is added, and the mixture is washed with DCM. The aqueous layer is adjusted to pH 10 using 2M aqueous NaOH, and extracted with DCM. The organic layer is dried over MgSO4, and the solvents are removed in vacuo. The crude mixture is purified using reversed phase HPLC to give the title compound; [M+H]+=424; 1H-NMR (400 MHz, CD3OD): δ 12.23 (s, 1H), 9.40 (d, 1H), 8.79 (d, 1H), 8.66 (d, 1H), 8.61 (t, 1H), 7.85 (t, 1H), 7.45 (t, 1H), 7.32 (d, 1H), 6.85 (m, 1H), 3.60 (s, 2H), 2.74 (s, 3H), 2.70-2.50 (m, 8H), 2.33 (s, 3H).

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