CN.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:9][C:10]1[N:14]([CH3:15])[N:13]=[CH:12][C:11]=1[C:16]1[N:17]=[C:18]([CH3:30])[N:19]2[C:24]=1[C:23]([N:25]1[CH:29]=NC=N1)=[N:22][CH:21]=[N:20]2>O1CCCC1.CN(C)C=O>[Br:9][C:10]1[N:14]([CH3:15])[N:13]=[CH:12][C:11]=1[C:16]1[N:17]=[C:18]([CH3:30])[N:19]2[C:24]=1[C:23]([NH:25][CH3:29])=[N:22][CH:21]=[N:20]2Methylamine (4.31 mL of a 2 M solution in tetrahydrofuran, 8.62 mmol) was added to a mixture of cesium carbonate (9.78 g, 30.0 mmol) and 5-(5-bromo-1-methyl-1H-pyrazol-4-yl)-7-methyl-4-(1H-1,2,4-triazol-1-yl)imidazo[5,1-f][1,2,4]triazine (from the previous reaction, 2.1 g) in N,N-dimethylformamide (12 mL), and the reaction was stirred at room temperature for 1 hour. It was quenched with a 1:1 mixture of water and saturated aqueous sodium chloride solution, then extracted with ethyl acetate (2×20 mL) and with tetrahydrofuran (10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide C4. Yield: 1.65 g, 5.12 mmol, 78% over 2 steps. LCMS m/z 322.1 (M+1). 1H NMR (500 MHz, CDCl3) δ 2.70 (s, 3H), 3.10 (d, J=4.9 Hz, 3H), 4.00 (s, 3H), 5.46-5.52 (m, 1H), 7.69 (s, 1H), 7.97 (s, 1H).
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