Cl.[NH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[OH:5].[Cl:13][C:14]1[CH:19]=[C:18](Cl)[N:17]=[CH:16][N:15]=1.C([O-])(O)=O.[Na+].O>O1CCOCC1>[Cl:13][C:14]1[N:15]=[CH:16][N:17]=[C:18]([NH:2][CH2:3][C@@H:4]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)[OH:5])[CH:19]=1A suspension of (R)-2-amino-1-(4-fluoro-phenyl)-ethanol hydrochloride (500 mg, 2.61 mmol), 4,6-dichloropyrimidine (353 mg, 2.37 mmol), and NaHCO3 (1.39 g, 16.6 mmol) in dioxane (10 mL) was heated in a 100° C. bath for 19 h and cooled to rt. Water (10 mL) was added, and the mixture, containing solid, was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (MgSO4) and concentrated. The residue was purified (FCC) to give the title compound as a white solid (415 mg, 59%) in 90% enantiomeric excess (Chiralcel AD-H column, supercritical CO2).
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