[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]2[N:13]=[C:12]3[NH:14][N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH:4]=[N:3]1.Br[C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:29])[S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>O1CCOCC1.CCOC(C)=O.[Cu](I)I>[CH3:29][N:24]([C:21]1[CH:22]=[CH:23][C:18]([N:14]2[C:12]3=[N:13][C:8]([NH:7][C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)=[N:9][CH:10]=[C:11]3[CH:16]=[N:15]2)=[CH:19][CH:20]=1)[S:25]([CH3:28])(=[O:26])=[O:27]A suspension of N-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-amine (see Example 1, step (i)) (60 mg, 0.28 mmol), N-(4-bromophenyl)-N-methylmethanesulfonamide (1.1 eq), copper iodide (0.1 eq), potassium phosphate (2 eq) and trans-1,2-diaminocyclohexane (0.1 eq) in dioxane (2 mL) was heated in the microwave at 160° C. for 2 h. After cooling to rt the mixture was diluted with EtOAc and washed with water. The organic phase was collected, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography (petroleum ether: EtOAc) to give the title product. 1H NMR (d6-DMSO) δ 10.07 (s, 1H), 9.03 (s, 1H), 8.33 (s, 1H), 8.19 (d, 2H), 7.97 (s, 1H), 7.66 (d, 2H), 7.60 (s, 1H), 3.84 (s, 3H), 3.01 (s, 3H); LC-MS method B, (ES+) 399.1, RT=8.18 min.
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