C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH:14]([OH:16])[CH3:15])[N:11]=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[N:9]=[CH:10][N:11]=[C:12]([CH:14]([OH:16])[CH3:15])[CH:13]=1A solution of [6-(1-hydroxyethyl)-pyrimidin-4-yl)-bis-carbamic acid tert-butyl ester and [6-(1-hydroxyethyl)-pyrimidin-4-yl)-carbamic acid tert-butyl ester (200 mg+198 mg, 1.45 mmol) in DCM (6.0 mL) was cooled to 0° C. and TFA (6.0 mL) was added. The reaction mixture was stirred at 0° C. for 15 minutes, then at room temperature for 2 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate solution and 2-methyltetrahydrofuran (×2). The aqueous layer was then extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-20% methanol in DCM) to afford the title compound as a colorless oil (195 mg, 96% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.60 (s, 1H), 8.54 (br s, 2H), 6.67 (s, 1H), 4.73-4.65 (m, 1H), 1.37 (d, J=6.6 Hz, 3H).
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