[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH2:16])[N:12]=[CH:11][C:10]=3[N:9]3[CH:17]=[N:18][N:19]=[C:8]3[C@H:7]2[CH2:20][CH3:21])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].ClC(OC)=O.[Cl-].[NH4+:30]>CN(C=O)C>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:2]4[CH:3]=[N:30][CH:4]=[CH:5][CH:1]=4)[N:12]=[CH:11][C:10]=3[N:9]3[CH:17]=[N:18][N:19]=[C:8]3[C@H:7]2[CH2:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5]1
To (R)-5-cyclopentyl-4-ethyl-4,5-dihydro-[1,2,4]triazolo[4,3-f]pteridin-7-amine (50 mg, 0.175 mmol) in DMF (1 ml) at 0° C. was added sodium hydride (60% in mineral oil, 7.7 mg, 0.193 mmol). The reaction mixture was stirred for 10 minutes, then methyl chloroformate (13.6 μL, 0.175 mmol) was added. The reaction was allowed to warm up to room temperature and was stirred for 18 hours. Ammonium chloride (5 ml, sat. aq. soln.) was added and extracted with EtOAc (3×10 ml). The combined organics were washed with brine (10 ml), dried over MgSO4, filtered and the solvent removed under vacuum. The crude product was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 M, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min] to afford the title compound as an off-white powder (25 mg, 31%).
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