Cl[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]2[CH3:20])[C:5]2[CH2:10][N:9]([CH:11]([CH3:13])[CH3:12])[CH2:8][C:6]=2[N:7]=1.[F:21][C:22]1[CH:23]=[C:24]([NH:37][C:38]([NH:40][CH2:41][CH2:42][OH:43])=[O:39])[CH:25]=[CH:26][C:27]=1B1OC(C)(C)C(C)(C)O1.ClCCl.C(=O)([O-])[O-].[Na+].[Na+].COC1CCCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CCO.O>[F:21][C:22]1[CH:23]=[C:24]([NH:37][C:38]([NH:40][CH2:41][CH2:42][OH:43])=[O:39])[CH:25]=[CH:26][C:27]=1[C:2]1[N:3]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][C@@H:15]2[CH3:20])[C:5]2[CH2:10][N:9]([CH:11]([CH3:13])[CH3:12])[CH2:8][C:6]=2[N:7]=1A solution of (S)-4-(2-chloro-6-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (intermediate 22) (109 mg, 0.367 mmol), 1-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2-hydroxyethyl)urea (intermediate 32) (151 mg, 0.466 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (15 mg, 0.018 mmol) and sodium carbonate (117 mg, 1.10 mmol) in 2 ml of a 7:3:1 mixture of CPME:H2O:EtOH respectively was heated in the microwave at 130° C. for 1 hour. The reaction was concentrated in vacuo and the residue redissolved in a mix of MeOH/DCM. It was loaded onto an SCX cartridge and washed with two column volumes of MeOH/DCM before being eluted with 2M NH3 in MeOH and concentrated in vacuo. The sample was then purified via preparative HPLC at high pH to yield the title compound (8 mg, 5%).
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