Reaction SMILES: Cl[C:2]1[CH:3]=[C:4]([C:17]2[N:25]=[C:24]([CH3:26])[N:23]=[C:22]3[C:18]=2[N:19]=[CH:20][N:21]3C2CCCCO2)[C:5]([NH:8][C:9]2[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)=[N:6][CH:7]=1.[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH2:40])=[CH:37][CH:36]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.Cl>C1COCC1.C([O-])(O)=O.[Na+].CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:33][O:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][NH:40][C:2]2[CH:3]=[C:4]([C:17]3[N:25]=[C:24]([CH3:26])[N:23]=[C:22]4[C:18]=3[N:19]=[CH:20][NH:21]4)[C:5]([NH:8][C:9]3[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)=[N:6][CH:7]=2)=[CH:37][CH:36]=1
Reactant: COc1ccc(CN)cc1
Reactant: COc1ccc(Nc2ncc(Cl)cc2-c2nc(C)nc3c2ncn3C2CCCCO2)cn1
Agent: [Pd]
Agent: CC(C)(C)[O-]
Agent: CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1
Solvent: CO
Solvent: C1CCOC1
Product: COc1ccc(CNc2cnc(Nc3ccc(OC)nc3)c(-c3nc(C)nc4[nH]cnc34)c2)cc1
Temperature: 100 °C
Reaction time: 8 h
Yield: 13 %

Procedure:
A solution of 5-chloro-N-(6-methoxypyridin-3-yl)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-amine (0.150 g, 0.332 mmol) and 4-methoxybenzylamine (0.108 mL, 0.830 mmol) (Source: Aldrich) in THF (10 mL) was treated with sodium tert-butoxide (0.096 g, 0.996 mmol) and 2-di-t-butylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (0.030 g). The mixture was deoxygenated and treated with Pd2(dba)3 (0.030 g, 0.033 mmol) under N2. The flask was fitted with a reflux condenser, then placed into a pre-heated bath at 80° C. and stirred overnight. The reaction mixture was diluted with saturated aqueous NaHCO3 (15 mL) and extracted with CH2Cl2 (2×25 mL). The combined organic extracts were washed with NaHCO3 (20 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give a tan oil. A glass microwave reaction vessel was charged with the crude oil and 1 N aqueous HCl (1.5 mL) in THF (2.5 mL). The reaction mixture was stirred and heated in a Discover model microwave reactor (CEM, Matthews, N.C.) at 100° C. for 8 min (100 watts, Powermax feature on). The mixture was diluted with MeOH, concentrated and neutralized with SiliCycle Si-Carbonate Silica Gel (SiliCycle Inc., Quebec City, Canada) (0.800 g). The mixture was diluted with THF/DCM (1:1) and allowed to stir under inert atmosphere overnight. The mixture was filtered and concentrated. The crude material was adsorbed onto a plug of silica gel and purified by chromatography through a RediSep®, Teledyne ISCO, Lincoln, Nebr., pre-packed silica gel column (40 g), eluting with a gradient of 1% to 15% isopropanol in dichloromethane to give N5-(4-methoxybenzyl)-N2-(6-methoxypyridin-3-yl)-3-(2-methyl-9H-purin-6-yl)pyridine-2,5-diamine (0.020 g, 0.043 mmol, 12.86% yield) as a tan solid. MS (ESI pos. ion) m/z 469 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 13.58 (s, 1H); 12.06 (s, 1H); 9.26 (s, 1H); 8.59-8.65 (m, 1H); 8.44 (d, J=2.15 Hz, 1H); 8.09 (dd, J=8.80, 2.35 Hz, 1H); 7.81 (d, J=2.54 Hz, 1H); 7.38 (d, J=8.41 Hz, 2H); 6.88 (d, J=8.61 Hz, 2H); 6.78 (d, J=8.80 Hz, 1H); 5.75 (s, 1H); 4.26 (s, 2H); 3.76-3.88 (m, 3H); 3.71 (s, 3H); 2.80-2.90 (m, 3H).