[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8](Cl)[CH:7]=[C:6]([Cl:11])[N:5]=1.[C:12]([O:16][C@@H:17]([C@H:19]1[CH2:23][O:22][C:21](=[O:24])[NH:20]1)[CH3:18])([CH3:15])([CH3:14])[CH3:13].CCOC(C)=O.CCCCCCC>CN(C=O)C.CCOC(C)=O>[C:12]([O:16][C@@H:17]([C@H:19]1[CH2:23][O:22][C:21](=[O:24])[N:20]1[C:8]1[CH:7]=[C:6]([Cl:11])[N:5]=[C:4]([Cl:3])[N:9]=1)[CH3:18])([CH3:13])([CH3:14])[CH3:15]
To a round bottom flask was added NaH (0.54 g, 13.5 mmol, 57% dispersion in mineral oil) to a solution of 2,4,6-trichloropyrimidine (1.22 ml, 10.6 mmol) and (R)-4-((R)-1-(tert-butoxy)ethyl)oxazolidin-2-one (1.8 g, 9.61 mmol) in DMF (32 mL) at 0° C. (ice bath) under a bubbler. The yellow suspension was then stirred at 0° C. for 15 min and then the ice bath was removed and reaction mixture allowed to stir 1 hr at room temperature. Reaction mixture was diluted with EtOAc and then carefully quenched with brine. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated onto silica gel. Silica gel column chromatography (EtOAc/Heptane 0 to 100%) provided (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2,6-dichloropyrimidin-4-yl)oxazolidin-2-one (2.1 g, 6.28 mmol, 65% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.04 (d, J=6.55 Hz, 3H) 1.26 (s, 9H) 4.38-4.48 (m, 2H) 4.64-4.75 (m, 2H) 8.22 (s, 1H). LCMS m/z 334.1 (M+H)+, Rt 1.10 min.
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