[F:1][C:2]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([Cl:11])[N:6]=1.[F:17][C:18]([F:24])([F:23])[CH2:19][CH2:20][CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:2][CH2:3][CH2:12][CH:13]([CH3:16])[CH3:14].[Cl:11][C:7]1[N:6]=[C:5]([N:4]([CH2:21][CH2:20][CH2:19][C:18]([F:24])([F:23])[F:17])[C:3]2[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:2]=2[F:1])[CH:10]=[CH:9][N:8]=14-(2-Fluoro-5-methylanilino)-2chloropyrimidine (Reference Example A-10, 750 mg, 3.16 mmol), 4,4,4-trifluoro-1-bromobutane (725 mg, 3.80 mmol) and potassium carbonate (525 mg, 3.80 mmol) were dissolved in DMF (3 ml). The reaction mixture was stirred at room temperature for 12 hours and then evaporated onto silica (5 ml) and purified by column chromatography eluting with EtOAc (0–40%):isohexane to give the title product as a solid on evaporation (976 mg). NMR (300 MHz, 373K): 1.79 (m, 2H), 2.28 (m, 2H), 2.33 (s, 3H), 3.91 (t, 2H), 6.19 (d, 1H), 7.28 (m, 3H), 8.03 (d, 1H); m/z (EI+) 347 (M+).
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