Cl.[F:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.[Na].[CH2:13]([O:15][C:16](=[O:25])[C:17]([C:22](=O)[CH3:23])=[CH:18]N(C)C)[CH3:14]>C(O)C>[CH2:13]([O:15][C:16]([C:17]1[C:22]([CH3:23])=[N:8][C:7]([C:6]2[CH:10]=[CH:11][C:3]([F:2])=[CH:4][CH:5]=2)=[N:9][CH:18]=1)=[O:25])[CH3:14]4-Fluorobenzamidine hydrochloride (1.25 g, 7.16 mmol) is added to a solution of sodium metal (0.17 g, 7.39 mmol) in dry ethanol (25 mL) and stirred at room temperature for 20 min. Ethyl-2-acetyl-3-(dimethylamino)acrylate (1.35 g, 7.16 mmol) is added. The mixture is heated to reflux for 3 hours. The solvent is removed in vacuo. The residue is dissolved in EtOAc, washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo to afford ethyl-2-(4-fluorophenyl)-4-methyl-pyrimidine-5-carboxylate (1.65 g, 87%) as a solid. MS: 261 (M+H) 261.
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