[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH2:8][C:6]=2[N:7]=1.[CH3:20][CH2:21][N:22](C(C)C)[CH:23]([CH3:25])[CH3:24].CC[O:31]C(C)=O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:21][CH2:20][O:31][CH2:24][C@@H:23]2[CH3:25])[C:5]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH2:8][C:6]=2[N:7]=1To a solution of tert-butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (1.00 g, 3.29 mmol) and DIPEA (1.21 mL, 6.97 mmol) at room temperature (20° C.) was added 3-S-methyl morpholine (0.54 g, 5.33 mmol). The reaction mixture was heated to 35° C. and stirred for 48 h. The reaction was diluted with DCM and Sat. NaHCO3. The organic layer was rinsed (brine), dried (anhydrous Na2SO4) and concentrated in vacuo. The desired product was isolated by flash chromatography (silica, 50 g, 0-50% EtOAc in petroleum ether (40-60) over 25 min) as a white solid (0.71 g, 1.92 mmol, 59% yield).
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