[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C@@H:9]([C:12]2O[CH:14]=[N:15][N:16]=2)[CH2:10][CH3:11])[C:5]([N+:22]([O-])=O)=[CH:4][N:3]=1.C(O)(=O)C>CO.[Zn]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:22]3[CH:14]=[N:15][N:16]=[C:12]3[C@@H:9]([CH2:10][CH3:11])[N:8]([CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:6]=2[N:7]=12-chloro-N-cyclopentyl-5-nitro-N-[(1R)-1-(1,3,4-oxadiazol-2-yl)propyl]pyrimidin-4-amine (37 mg, 0.1049 mmol) in methanol (1.850 mL) was treated with zinc (116.6 mg, 16.35 μL, 1.783 mmol) and then dropwise acetic acid (245.7 mg, 232.7 μL, 4.091 mmol). The reaction was stirred at ambient temperature for 10 minutes. The reaction was filtered and the residual zinc washed with methanol. The combined filtrates were concentrated and re-dissolved in acetic acid (2 mL) and stirred at 70° C. for 1 hour. The reaction was filtered and precipitate washed with methanol. The filtrates were concentrated to dryness under reduced pressure, taken into 10% MeOH/DCM and passed through a short silica gel column. The residue was trituated with ether and the title compound isolated by filtration as a pale brown solid (21 mg, 66%); 1H NMR (400.0 MHz, DMSO) d 0.75 (3H, t), 1.50-1.64 (2H, m), 1.80-2.08 (8H, m), 4.22-4.33 (1H, m), 5.28-5.35 (1H, m), 8.68 (1H, s), 9.35 (1H, s); MS ES (+) 305.7.
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