[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[NH:13][C:12](=[O:14])[C:9]3([CH2:11][CH2:10]3)[CH2:8][N:7]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:6]=2[N:20]=1.IC.[C:23](=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:13]([CH3:23])[C:12](=[O:14])[C:9]3([CH2:11][CH2:10]3)[CH2:8][N:7]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:6]=2[N:20]=1To a solution of 1.00 g (0.0034 mole) of 2-chloro-9-cyclopentyl-8,9-dihydro-spiro[5H-pyrimido[4,5-b][1,4]diazepine-7,1′-cyclopropan]-6(7H)-one (VI-53) in 40 mL of dimethylformamide was added 1.47 g (0.0104 mole) of iodomethane and 1.68 g (0.00575 mole) of cesium carbonate. The mixture was stirred at ambient temperature overnight and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 0.957 g of 2-chloro-9-cyclopentyl-8,9-dihydro-5-methylspiro[5H-pyrimido[4,5-b][1,4]diazepine-7,1′-cyclopropan]-6(7H)-one (VII-53) as a white solid.
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