[H-].[Na+].[CH2:3]([CH:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C:5]#[CH:6].Cl[C:21]1[N:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][N:22]=1>CN(C=O)C.CCOC(C)=O>[CH2:3]([C:7]([C:21]1[N:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][N:22]=1)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C:5]#[CH:6]A suspension of NaH (60%, 2.5 g, 62.4 mmol) in 100 mL of DMF was added tert-butyl ethyl but-3-yn-1-ylpropanedioate (15 g, 62.4 mmol) drop-wise at 25° C. The mixture was stirred at 40° C. for 30 minutes and 2-chloro-5-nitropyrimidine (10.0 g, 62.4 mmol) in 50 mL of DMF was added dropwise. The resulting suspension was stirred at 50° C. for 2 hours and diluted with 500 mL of EtOAc. The mixture was washed with water (3×100 mL), brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography (Petroleum ether:EtOAc=10:1) to afford the title compound; MS m/z 364 (M+1)+.
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