Br.Br.Br[CH2:4][C:5]1[C:6]([NH2:14])=[N:7][C:8]([CH2:11][CH2:12][CH3:13])=[N:9][CH:10]=1.Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH2:28][CH2:27][N:26]([CH2:4][C:5]3[C:6]([NH2:14])=[N:7][C:8]([CH2:11][CH2:12][CH3:13])=[N:9][CH:10]=3)[CH2:25][CH:24]=2)=[CH:19][CH:18]=1A suspension of 7.0 g (0.020 mol) of 5-bromomethyl-2-propyl-pyrimidin-4-ylamine dihydrobromide, 4.2 g (0.020 mol) of 4-(4-fluoro-phenyl)-1,2,3,6-tetrahydropyridine hydrochloride and 8.0 g (0.060 mol) of dry potassium carbonate in 60 ml of dimethylformamide was stirred at room temperature for 18 hours. The mixture was suction filtered, the filter cake was washed with dichloromethane, the filtrate was completely freed from the solvents and the residue was recrystallized twice from ethyl acetate/cyclohexane and then from hot ethanol. 1.4 g (21%) of 5-[4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridin-1-ylmethyl]-2-propyl-pyrimidin-4-ylamine were obtained as white crystals; m.p. 142°-145°.
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