[NH2:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].O>C(Cl)Cl.CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>[NH2:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1
To a suspension of 2-amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (336.7 mg, 2.0 mmol) in CH2Cl2 (14.3 mL) was added benzyl bromide (0.26 mL, 2.2 mmol) and TBABr (644 mg, 2.0 mmol). The reaction mixture was cooled to 0° C., and to it was added 50% NaOH (1.7 mL). The resulting mixture was stirred for 2 h as it warmed from 0° C. to room temperature. Water was then added, and the solution was washed with CHCl3. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by column chromatography, eluting with CH2Cl2/Acetone (5:1-1:1), afforded the product as a tan solid (423 mg, 82%)
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