Reaction SMILES: COC1C=CC(C[O:8][CH2:9][C:10]2[CH:11]=[C:12]([C:32]3[N:40]=[C:39]([CH3:41])[N:38]=[C:37]4[C:33]=3[N:34]=[CH:35][N:36]4C3CCCCO3)[C:13]([NH:16][C:17]3[C:18]4[CH:19]=[N:20][N:21](C5CCCCO5)[C:22]=4[CH:23]=[CH:24][CH:25]=3)=[N:14][CH:15]=2)=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:21]1[C:22]2[C:18](=[C:17]([NH:16][C:13]3[N:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][C:12]=3[C:32]3[N:40]=[C:39]([CH3:41])[N:38]=[C:37]4[C:33]=3[N:34]=[CH:35][NH:36]4)[CH:25]=[CH:24][CH:23]=2)[CH:19]=[N:20]1
Reactant: COc1ccc(COCc2cnc(Nc3cccc4c3cnn4C3CCCCO3)c(-c3nc(C)nc4c3ncn4C3CCCCO3)c2)cc1
Solvent: O=C(O)C(F)(F)F
Solvent: ClCCl
Product: Cc1nc(-c2cc(CO)cnc2Nc2cccc3[nH]ncc23)c2nc[nH]c2n1
Temperature: 25 °C
Reaction time: 2 h
Yield: 150.4 %

Procedure:
N-(5-((4-Methoxybenzyloxy)methyl)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-amine (19.8 mg, 0.0300 mmol) was dissolved in DCM (1.0 mL) and TFA (0.10 mL) was added and the reaction was stirred at room temperature. After 2 hours, more TFA (0.15 mL) was added, and stirring was continued. After another hour, the reaction was quenched with saturated sodium bicarbonate (3.8 mL), and the reaction was stirred for about 10 minutes. In a separate flask, N-(5-((4-methoxybenzyloxy)methyl)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-amine (178.5 mg, 0.2701 mmol) was dissolved in DCM (5.0 mL) and TFA (0.50 mL) was added. The reaction was stirred at room temperature for 3.5 hours, and then more TFA (0.75 mL) was added, and stirring was continued. After another hour, more TFA (0.80 mL) was added, and stirring was continued. After 45 minutes, the reaction was diluted with DCM (5 mL) and quenched with saturated sodium bicarbonate (30 mL). At this point, both reactions were combined and allowed to stand overnight. The layers were separated and brine was added to help break up emulsions. The aqueous phase was extracted with 10:1 DCM/MeOH. However, both the organic extracts and the aqueous phase were found by LCMS to contain product. So, they were combined, concentrated, and treated with 10:1 DCM/MeOH and filtered. The solid was washed with DCM and MeOH. The filtrate was concentrated and treated with DCM and MeOH and filtered again. The filtrate again was concentrated and dried briefly under high vacuum, then redissolved in DCM and MeOH and concentrated and dried on high vacuum over the weekend. The material was dissolved in MeOH and DMSO, concentrated, and washed repeatedly with Et2O, and these washings were discarded. Then, the material was dissolved in EtOAc and MeOH, concentrated, treated with water, and filtered. The solid was washed with water, collected and set aside. The filtrate was filtered again (solid had precipitated out), and this solid was washed with water. The filtrate from this second filtration was discarded, and the two sets of solid were collected, treated with MeOH, and filtered. The solid was not pure by LCMS, so the filtrate and solid were combined, concentrated, and purified by HPLC (10% to 100% MeCN/water with 0.1% TFA over 30 minutes with a total flow rate of 100 mL/min). The fractions with product were collected, concentrated, and dried under high vacuum in a water bath (about 50° C.). Then, the solid was washed with DCM and repurified on HPLC (10% to 100% MeCN/water with 0.1% TFA over 30 minutes with a total flow rate of 100 mL/min) to give (6-(1H-indazol-4-ylamino)-5-(2-methyl-9H-purin-6-yl)pyridin-3-yl)methanol (16.8 mg, 17% yield). MS (ESI pos. ion) m/z 373 (M+H)+. 1H NMR (d6-DMSO) δ 12.71 (s, 1H), 9.80 (s, 1H), 8.66 (s, 1H), 8.34 (d, J=1.96 Hz, 1H), 8.26 (s, 1H), 8.07 (d, J=7.82 Hz, 1H), 7.33 (t, J=8.4 Hz, 1H), 7.18 (d, J=8.41 Hz, 1H), 4.56 (s, 2H), 2.94 (s, 3H).