Reaction SMILES: [CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([CH2:7][N:8]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH:23]([N:25]4[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][C@H:26]4[CH3:38])[CH3:24])[CH:19]=[N:20][C:21]=3F)[N:10]=2)=[CH:5][CH:4]=1.[F:50][C:51]1[CH:52]=[C:53]([NH2:59])[CH:54]=[N:55][C:56]=1[O:57][CH3:58].O1CCCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>>[CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([CH2:7][N:8]([CH2:39][C:40]2[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([C@H:23]([N:25]4[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[CH2:27][C@H:26]4[CH3:38])[CH3:24])[CH:19]=[N:20][C:21]=3[NH:59][C:53]3[CH:54]=[N:55][C:56]([O:57][CH3:58])=[C:51]([F:50])[CH:52]=3)[N:10]=2)=[CH:5][CH:4]=1.[CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([CH2:7][N:8]([CH2:39][C:40]2[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([C@@H:23]([N:25]4[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:35])([CH3:36])[CH3:37])=[O:32])[CH2:27][C@H:26]4[CH3:38])[CH3:24])[CH:19]=[N:20][C:21]=3[NH:59][C:53]3[CH:54]=[N:55][C:56]([O:57][CH3:58])=[C:51]([F:50])[CH:52]=3)[N:10]=2)=[CH:5][CH:4]=1
Reactant: COc1ncc(N)cc1F
Reactant: COc1ccc(CN(Cc2ccc(OC)cc2)c2nc(C)nc(-c3cc(C(C)N4CCN(C(=O)OC(C)(C)C)C[C@H]4C)cnc3F)n2)cc1
Agent: C[Si](C)(C)[N-][Si](C)(C)C
Agent: [Li+]
Solvent: C1CCOC1
Product: COc1ccc(CN(Cc2ccc(OC)cc2)c2nc(C)nc(-c3cc([C@@H](C)N4CCN(C(=O)OC(C)(C)C)C[C@H]4C)cnc3Nc3cnc(OC)c(F)c3)n2)cc1
Product: COc1ccc(CN(Cc2ccc(OC)cc2)c2nc(C)nc(-c3cc([C@H](C)N4CCN(C(=O)OC(C)(C)C)C[C@H]4C)cnc3Nc3cnc(OC)c(F)c3)n2)cc1
Temperature: -40 °C
Yield: 38.1 %
Yield: 29.6 %

Procedure:
To a 250 mL round-bottomed flask was added (3R)-tert-butyl 4-(1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-fluoropyridin-3-yl)ethyl)-3-methylpiperazine-1-carboxylate (1.0 g, 1.489 mmol), 5-fluoro-6-methoxypyridin-3-amine (0.317 g, 2.233 mmol) (Anichem), tetrahydrofuran (20 mL, 247 mmol). The solution was stirred at −40° C. and treated dropwise via addition funnel with lithium bis(trimethylsily)amide (Aldrich) (4.47 mL, 4.47 mmol). The solution was stirred at −40° C. for 30 minutes and quenched with water and NH4Cl (20 ml) each and diluted with EtOAc (20 mL) and the aqueous layer was extracted with EtOAc (2×20 mL). The organic extract was washed with saturated NaCl (20 mL) and dried over sodium sulfate, filtered and concentrated in vacuum. The crude product was adsorbed onto a plug of silica gel and chromatographed through a silica gel column (40 g), eluting with a gradient of 5% to 50% EtOAc in hexane, to provide (R)-tert-butyl 4-((R)-1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethyl)-3-methylpiperazine-1-carboxylate (0.45 g, 0.567 mmol, 38.1% yield), and (R)-tert-butyl 4-((S)-1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethyl)-3-methylpiperazine-1-carboxylate (0.35 g, 0.441 mmol, 29.6% yield).