Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.[F:15][C:16]1[CH:17]=[C:18]2[C:24]([NH2:25])=[N:23][NH:22][C:19]2=[N:20][CH:21]=1.C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O>[Cl:8][C:6]1[N:5]=[C:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=[C:2]([NH:25][C:24]2[C:18]3[C:19](=[N:20][CH:21]=[C:16]([F:15])[CH:17]=3)[NH:22][N:23]=2)[CH:7]=1A mixture cooled to −60° C. containing 4,6-dichloro-2-cyclohexylpyrimidine (505 mg, 2.19 mmol), 5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine (400 mg, 2.63 mmol) and THF (20 mL) was treated drop wise with a 1M solution of lithium bis(trimethylsilyl)amide in THF (5.46 mL, 5.46 mmol). The reaction mixture was then allowed to warm to 0° C. over 1 h before water was added. The reaction mixture partitioned between water and EtOAc, washed with sat. NaCl solution and dried (Na2SO4) and concentrated in-vacuo. The resulting residue was purified by column chromatography (eluting with MeOH/DCM, 5/95) to give the title compound as a solid (380 mg, 50%). MS (ES+) m/e=347. 1H NMR: (DMSO) 1.10-1.96 (10H, m), 2.56-2.69 (1H, m), 7.65 (1H, brs), 8.27-8.39 (1H, m), 8.58 (1H, s), 10.72 (1H, s), 13.34 (1H, s).
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