[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][N:10]([CH3:12])[CH2:9][CH:8]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:6]=2[N:7]=1.[CH3:21][NH:22][CH2:23][CH:24]=[CH2:25].O>CN1C(=O)CCC1>[CH2:23]([N:22]([CH3:21])[C:4]1[C:5]2[CH2:11][N:10]([CH3:12])[CH2:9][CH:8]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:6]=2[N:7]=[C:2]([Cl:1])[N:3]=1)[CH:24]=[CH2:25]The mixture of 2,4-dichloro-8-(4-fluorophenyl)-6-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (Preparation V, 408 mg, 1.307 mmol) in NMP (13 mL) was added N-methylprop-2-en-1-amine (465 mg, 6.53 mmol). The resulting reaction mixture was stirred at rt overnight. Water (50 mL) was added to the mixture and stirred for 30 min. The mixture was filtered to get a light tan solid which was dried and purified by flash column chromatography eluting with 30 to 100% EtOAc/Hexane to get N-allyl-2-chloro-8-(4-fluorophenyl)-N,6-dimethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (453 mg, 100% yield). LC-MS (M+H)+=347.1.
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