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At room temperature, N,N-dimethylformamide dimethylacetal (30 ml) was added to 1-(tert-butoxycarbonyl)-3-pyrrolidone (4.57 g) The resulting mixture was heated at 140C for 1 hour. After the reaction mixture was allowed to cool down to room temperature, it was concentrated under reduced pressure. Hexane was added to the residue and a yellow powder thus precipitated was collected by filtration. The powder was dissolved in ethanol (100 ml). Methylisothiourea sulfate (9.24 g) and sodium ethoxide (4.52 g) were added to the resulting solution at room temperature. The resulting mixture was heated under reflux for 24 hours. Saturated saline and diethyl ether were added to the reaction mixture to separate the layers. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography (methanol:methylene chloride = 1:99) on a silica gel column, whereby the title compound (1.10 g) was obtained.1H-NMR (CDCl3) delta: 1.51(9H,s), 2.57(3H,m), 4.15-4.45(4H,m), 8.39(1/2H,s), 8.43(1/2H,s). MS (FAB) m/z: 268 (M+H)+.
[Referential Example 47] tert-Butyl 2-(methylsulfanyl)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate: 1-tert-Butoxycarbonyl-3-pyrrolidone (4.57 g) was added to N,N-dimethylformamide dimethyl acetal (30 ml) at room temperature, and the mixture was heated for 1 hour at 140C. After allowing the reaction mixture to cool to room temperature, it was concentrated under reduced pressure.. hexane was added to the residue, and yellow powder deposited was collected by filtration.. This powder was dissolved in ethanol (100 ml), and methylisothiourea sulfate (9.24 g) and sodium ethoxide (4.52 g) were added to the resultant solution at room temperature, and the mixture was heated under reflux for 24 hours.. Saturated aqueous solution of sodium chloride and diethyl ether were added to the reaction mixture to separate an organic layer.. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol: methylene chloride = 1:99) to obtain the title compound (1.10 g).1H-NMR (CDCl3) delta: 1.51(9H,s), 2.57(3H,m), 4.15-4.45(4H,m), 8.39(1/2H,s), 8.43(1/2H,s). MS (FAB) m/z: 268(M+H)+.
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