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:36]=[C:37]([CH:39]=[CH:40][CH:41]=1)[NH2:38].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:36]=[C:37]([NH:38][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:39]=[CH:40][CH:41]=1
Reactant: COc1ccc(Nc2ncc(Cl)cc2-c2nc(C)nc3c2ncn3C2CCCCO2)cn1
Reactant: COc1cccc(N)c1
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: COc1cccc(Nc2cnc(Nc3ccc(OC)nc3)c(-c3nc(C)nc4[nH]cnc34)c2)c1
Temperature: 100 °C
Reaction time: 8 h
Yield: 17.3 %

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 (0.230 g, 0.509 mmol) and 3-methoxyaniline (0.142 mL, 1.272 mmol) (Aldrich, St. Louis, Mo.) in THF (10 mL) was treated with sodium tert-butoxide (0.147 g, 1.527 mmol) and 2-di-t-butylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (0.040 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 triturated with THF. The precipitate was collected by filtration and washed with diethyl ether (3×25 ml). The solid (0.178 g) was neutralized with SiliCycle Si-Carbonate Silica Gel (SiliCycle Inc., Quebec City, Canada) (1.8 g) in a mixture of THF/DCM (1:1; 10 mL) and allowed to stir under inert atmosphere overnight. The mixture was filtered with a fine-fritted funnel. The desired material which was still attached to the Silica-polymer, was released by washing the silica with methanol (2×10 mL) and concentrated. The residue was triturated with diethyl ether and the precipitate was collected by filtration to give N5-(3-methoxyphenyl)-N2-(6-methoxypyridin-3-yl)-3-(2-methyl-9H-purin-6-yl)pyridine-2,5-diamine (0.040 g, 0.088 mmol, 17.29% yield) as a tan solid. MS (ESI pos. ion) m/z 456 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 12.50 (s, 1H); 9.75 (s, 1H); 8.54 (s, 2H); 8.17 (s, 2H); 8.08 (s, 1H); 7.08 (s, 1H); 6.83 (d, J=8.80 Hz, 1H); 6.51-6.59 (m, 2H); 6.32 (s, 1H); 3.84 (s, 3H); 3.71 (s, 3H); 2.86 (s, 3H).