[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:18][CH2:17][C:11]3[N:12]=[CH:13][NH:14][C:15](=O)[C:10]=3[CH2:9]2)=[N:6][CH:7]=1.P(Cl)(Cl)([Cl:21])=O.ClCCCl.CN(C)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:21][C:15]1[C:10]2[CH2:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=3)[CH2:18][CH2:17][C:11]=2[N:12]=[CH:13][N:14]=1Into a 250 ml round bottom flask was combined 5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidin-4(3H)-one (0.250 g, 0.00103 mol), phosphoryl chloride (0.8 mL, 0.008 mol), and 1,2-dichloroethane (10 mL, 0.1 mol). N,N-Dimethylaniline (0.01 g, 0.0001 mol) was added dropwise and the mixture was heated at reflux for 2 hours. The mixture was reduced in vacuo to yield a dark brown oil. The oil was taken up in methylene chloride (50 ml) and poured over ice. The mixture was carefully neutralized using sat sodium bicarbonate. The layers were separated and the organic was dried over sodium sulfate and reduced in vacuo. The mixture was purified by flash chromatography on silica gel using methylene chloride:methanol (0-10%). The combined pure fractions were reduced in vacuo to yield a bright yellow solid. (0.141 g, 52.4%).
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