[OH:1][C@@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].Cl[C:10]1[C:11]2[N:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:12]=2[N:13]=[C:14]([NH:16]C(=O)C)[N:15]=1>C1COCC1>[Cl:24][C:22]1[CH:21]=[CH:20][C:12]2[N:13]=[C:14]([NH2:16])[N:15]=[C:10]([O:1][CH:2]3[CH2:6][CH2:5][O:4][CH2:3]3)[C:11]=2[N:23]=1(R)-(−)-3-hydroxy-tetrahydrofuran (0.62 mL) was added to a suspension of NaH (0.31 g, 7.7 mmol) in THF (15 mL). After stirring for 1 hour, the resulting mixture was added to a suspension of N-(4,6-dichloro-pyrido[3,2-d]pyrimidin-2-yl)-acetamide (0.9 g, 3.5 mmol) in THF (15 mL). The mixture was stirred at room temperature for 20 minutes, then diluted with EtOAC (100 mL) and washed with brine. The organic layer was dried over Na2SO4 and concentrated to afford 6-chloro-4-(tetrahydro-furan-3-yloxy)-pyrido[3,2-d]pyrimidin-2-ylamine as a yellow solid (0.55 g, yield: 51%) which was characterized by its mass spectrum as follows: MS (m/z) 309.1 [M+H]+.
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