[NH2:1][C:2]1[NH:3][C:4](=[O:13])[C:5]2[C:10]([I:11])=[CH:9][N:8]([CH3:12])[C:6]=2[N:7]=1.[H-].[Na+].I[CH3:17]>CN(C)C=O.O>[NH2:1][C:2]1[N:3]([CH3:17])[C:4](=[O:13])[C:5]2[C:10]([I:11])=[CH:9][N:8]([CH3:12])[C:6]=2[N:7]=1To a solution of 2-amino-5-iodo-7-methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (15.4 g, 53.1 mmol) in N,N-dimethylformamide (150 ml) was added sodium hydride (66% dispersion in oil, 1.93 g, 53.1 mmol) and iodomethane (3.31 ml, 53.1 mmol) at 0° C., and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was diluted with water and extracted with ethyl acetate (×2) and ethyl acetate-tetrahydrofuran (×2). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 50-100% hexane/ethyl acetate gradient mixture, and the desired fractions were concentrated in vacuo. The residual crystals were washed with diethyl ether to give 12.3 g (76%) of the title compound.
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