Acetonitrile → HCID 178439997, compound
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:25][C@H:24]([CH2:26][O:27][C:28]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)=[O:29])[C@@H:13]([O:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[O:16])[CH2:12]2)=[C:4]([N:37]2[CH:41]=[CH:40][N:39]=[C:38]2[CH2:42][CH2:43][CH3:44])[N:3]=1.[CH2:45]([I:52])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.CC#N>>[I-:52].[CH2:45]([N:39]1[CH:40]=[CH:41][N+:37]([C:4]2[N:3]=[C:2]([Cl:1])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[C@@H:11]2[O:25][C@H:24]([CH2:26][O:27][C:28]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)=[O:29])[C@@H:13]([O:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[O:16])[CH2:12]2)=[C:38]1[CH2:42][CH2:43][CH3:44])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1Participants
Procedure
2-Chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-propylimidazol-1-yl)purine (0.615 g, 1 mmol) was treated with a solution of BnI in CH3CN (0.3 M, 40 mL, 12 mmol) by method 3 to give 3-benzyl-1-{2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]purin-6-yl}-2-propylimidazolium iodide (0.83 g, crude): 1H NMR (500 MHz, CDCl3) δ 8.94 (s, 1H), 8.49 (s, 1H), 8.00 (d, J=8.5 Hz, 2H), 7.88 (d, J=8.0 Hz, 2H), 7.81 (s, 1H), 7.46-7.50 (m, 5H), 7.32 (d, J=8.0 Hz, 2H), 7.25 (d, J=8.0 Hz, 2H), 6.67 (t, J=7.3 Hz, 1H), 5.75-5.85 (m, 3H), 4.71-4.82 (m, 3H), 3.67-3.74 (m, 2H), 2.99-3.02 (m, 2H), 2.47 (s, 3H), 2.42 (s, 3H), 1.75-1.81 (m, 2H), 1.17 (t, J=7.5 Hz, 3H); HRMS m/z 705.2606 (M+[C39H38ClN6O5=705.2592]).
Sources & evidence
- ORD record
- ord-a640059402774ab39eff1d9d7ef81a77
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855285B2
Reaction notes
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