[NH:1]1[CH2:6][CH2:5][CH:4]([C@H:7]2[CH2:9][C@H:8]2[CH2:10][CH2:11][OH:12])[CH2:3][CH2:2]1.Cl[C:14]1[N:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O.CCOC(C)=O.O>[CH2:21]([O:20][C:17]1[CH:16]=[N:15][C:14]([N:1]2[CH2:6][CH2:5][CH:4]([C@H:7]3[CH2:9][C@H:8]3[CH2:10][CH2:11][OH:12])[CH2:3][CH2:2]2)=[N:19][CH:18]=1)[CH3:22]2-((1S,2R)-2-(piperidin-4-yl)cyclopropyl)ethanol (4.0 g, 23.6 mmol) and 2-chloro-5-ethoxypyrimidine (4.12 g, 26.0 mmol) were dissolved in 40 mL of DMA, to which was added cesium carbonate (10.0 g, 30.7 mmol). The reaction was heated at 105° C. overnight. The reaction mixture was cooled to rt and diluted with 40 mL of EtOAc and 40 mL of water. The layers were separated and the aqueous phase extracted with EtOAc (30 mL×2). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (KP-Sil 340 g SNAP column, Biotage system) eluting with 15-80% EtOAc:hexanes over 11 CV to afford the title compound. LC/MS (m/z): 292 (M+H)+.
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