[H-].[Na+].[Cl:3][C:4]1[N:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[C:11]([CH3:16])([CH3:15])[CH2:10][N:9]([C@@H:17]3[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]3)[C:8]=2[N:24]=1.[CH3:25]I>CC(N(C)C)=O>[Cl:3][C:4]1[N:5]=[CH:6][C:7]2[N:13]([CH3:25])[C:12](=[O:14])[C:11]([CH3:16])([CH3:15])[CH2:10][N:9]([C@@H:17]3[CH2:21][CH2:20][C:19]([F:23])([F:22])[CH2:18]3)[C:8]=2[N:24]=160% Sodium hydride in mineral oil (0.210 g, 5.24 mmol) was added to a mixture of (R)-2-chloro-9-(3,3-difluorocyclopentyl)-7,7-dimethyl-8,9-dihydro-5H-pyrimido[4,5-b][1,4]diazepin-6(7H)-one (1.65 g, 4.99 mmol) and methyl iodide (0.34 ml, 5.49 mmol) in dimethylacetamide (18 mL). The reaction mixture was stirred at room temperature for 25 minutes. Ice was added to the reaction mixture and the resultant precipitate collected and rinsed with water. The solid was dried in a pistol in vacuo for 3 hours. The title compound was obtained as a white solid (1.68 g, 98% yield).
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