[CH2:1]([N:4]1[C:12]2C(Cl)=NC=[N:8][C:7]=2[CH:6]=[CH:5]1)[CH:2]=[CH2:3].[H-].[Na+].CI.[CH3:18][N:19]([CH:21]=[O:22])[CH3:20]>O>[CH2:1]([N:4]1[C:12]2[C:21](=[O:22])[N:19]([CH3:20])[CH:18]=[N:8][C:7]=2[CH:6]=[CH:5]1)[CH:2]=[CH2:3]To a room temperature solution of 5-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidine (220 mg, 1.3 mmol, 1 equiv.) in 3 mL of DMF was added 60% NaH (100 mg, 2.5 mmol, 2 equiv.) followed by MeI (0.18 ml, 1.8 mmol, 1.5 equiv.). After 30 minutes, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by reverse phase HPLC (5-90% CH3CN/water+0.1% TFA). The desired fractions were combined and concentrated to remove CH3CN. The remaining aqueous mixture was extracted with EtOAc, dried, filtered, and evaporated to provide 152 mg (64%) of 5-allyl-3-methyl-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one as a yellow oil which was used without further purification.
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