C(OC([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]1[N:20]=[C:19](SC)[C:18]([F:23])=[CH:17][N:16]=1)=O)(C)(C)C.ClC1N=C(SC)C(F)=CN=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[F:23][C:18]1[CH:17]=[N:16][C:15]([N:11]2[CH2:10][C@@H:9]3[CH2:14][C@H:12]2[CH2:13][NH:8]3)=[N:20][CH:19]=12-(t-butyloxycarbonyl)-5-(5-fluoro-4-methylthio-2-pyrimidinyl)-(1S,4S)-2,5-diazabicyclo[2.2.1]heptane (4.50 g, 22.73 mmol), 2-chloro-5-fluoro-4-methylthiopyrimidine [4.64 g (87.5% pure), 22.73 mmol], micropulverized K2CO3 (9.40 g, 68.19 mmol), and KI (0.57 g, 3.41 mmol) in 65 mL of MeCN was refluxed for 44 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in a minimum amount of H2O. The solution was extracted with CH2Cl2, washed with saturated NaCl solution, dried over K2CO3, filtered and concentrated under reduced pressured. Flash chromatography (Hexane:EtOAc; 4:1) gave the title compound (6.60 g, 85.4%).
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