[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:19]I>O1CCCC1.[Cl-].[Na+].O>[Si:10]([O:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][CH3:19])[N:7]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:11])[CH3:12]Under a nitrogen atmosphere, a solution of 2-amino-4-(tert-butyldimethylsilyloxymethyl)pyrimidine (200 mg, 0.84 mmol, Reference Compound No. 5-1) in anhydrous tetrahydrofuran (4.0 mL) was added dropwise to a suspension of sodium hydride (60%, 37 mg, 0.92 mmol) in anhydrous tetrahydrofuran (1.0 mL) under ice-cooling. The mixture was stirred for 15 minutes under ice-cooling, then methyl iodide (57 μL, 0.92 mmol) was added thereto, and the mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into brine (30 mL), then extracted with ethyl acetate (30 mL). The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give 43 mg of the title Reference Compound as a colorless oil (Yield: 20%).
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