Reaction SMILES: [NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]3[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl.O>[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([C@@H:24]3[CH2:29][CH2:28][C@H:27]([N:35]4[CH2:36][CH2:37][CH:32]([OH:31])[CH2:33][CH2:34]4)[CH2:26][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([C@H:24]3[CH2:29][CH2:28][C@H:27]([N:35]4[CH2:36][CH2:37][CH:32]([OH:31])[CH2:33][CH2:34]4)[CH2:26][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1
Reactant: Nc1ncnc2c1c(-c1ccc(Oc3ccccc3)cc1)cn2C1CCC(=O)CC1
Reactant: OC1CCNCC1
Agent: CC(=O)O[BH-](OC(C)=O)OC(C)=O
Agent: O=C([O-])O
Agent: [Na+]
Solvent: ClCCCl
Solvent: O
Solvent: CC(=O)O
Product: Nc1ncnc2c1c(-c1ccc(Oc3ccccc3)cc1)cn2[C@H]1CC[C@@H](N2CCC(O)CC2)CC1
Product: Nc1ncnc2c1c(-c1ccc(Oc3ccccc3)cc1)cn2[C@H]1CC[C@H](N2CCC(O)CC2)CC1
Temperature: 80 °C
Reaction time: 58 h

Procedure:
A mixture of 4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexanone (0.997 g, 2.50 mmol), 4-hydroxypiperidine (0.760 g, 7.5 mmol), sodium triacetoxyborohydride (0.689 g, 3.25 mmol), and acetic acid (0.43 mL, 7.5 mmol) in 1,2-dichloroethane (50 mL) was stirred at 80° C. under an atmosphere of nitrogen for 58 hours. The reaction mixture was cooled and water (50 mL) and sodium bicarbonate (1.35 g, 16.1 mmol) were added and the mixture was stirred for 2 hours. The organic layer was separated, dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure to yield a brown solid. The cis and trans isomers were purified by flash chromatography on silica gel (1 L 5% MeOH in CH2Cl2, then 500 mL 10% MeOH in CH2Cl2, 500 mL 50:45:5 CH2Cl2:MeOH:Et3N, and 500 mL 45:45:10 CH2Cl2:MeOH:Et3N). In order to remove residual Et3N, each of the products was taken up in CH2Cl2, washed with 40 mL water, the organic portion separated, dried over magnesium sulfate, filtered, and concentrated to yield cis-1-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}-4-piperidinol as a brown solid (0.185 g, 0.382 mmol) and trans-1-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}-4-piperidinol as a brown solid (0.115 g, 0.237 mmol). The cis-1-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}-4-piperidinol (0.185 g, 0.383 mmol) was dissolved in warm ethyl acetate (5 mL) then added to a solution of maleic acid (0.089 g, 0.765 mmol) in ethanol (5 mL). The mixture was cooled to ambient temperature and the solid was collected by filtration and dried to give cis-1-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}-4-piperidinol dimaleate salt (0.202 g) as a yellow solid: 1H NMR (d6 DMSO, 400 MHz): δ H 8.61(1H, bs), 8.25(1H, s), 7.40-7.56(5H, m), 7.08-7.19(5H, m), 6.40 (2H, bs), 6.13(4H, s), 5.00-5.20(1H, m), 4.80 (1H, m), 3.03-3.95(9H, m), 2.30-2.32(2H, m), 1.63-1.99(6H, m); RP-HPLC (Delta Pak C18, 5 μm, 300 A, 15 cm; 5%-85% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 13.33 min. MS: MH+ 484.