4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → (S)-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)aniline
Reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)O1.Cl[C:18]1[N:19]=[C:20]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][C@@H:29]2[CH3:34])[C:21]2[CH2:26][N:25]([CH3:27])[CH2:24][C:22]=2[N:23]=1>>[CH3:27][N:25]1[CH2:26][C:21]2[C:20]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][C@@H:29]3[CH3:34])=[N:19][C:18]([C:9]3[CH:10]=[CH:11][C:12]([NH2:13])=[CH:14][CH:15]=3)=[N:23][C:22]=2[CH2:24]1Participants
3
Procedure
Step 2 Method as intermediate 5, using 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline and (S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine. The crude reaction mixture was partitioned between water and EtOAc, the phases separated and the organic layer dried over magnesium sulphate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (0-15% MeOH/DCM), to yield a pale yellow oil (477 mg, 72%).