Ammonium Hydroxide → [(E)-2-[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]vinyl]phosphonic acid
Reaction equation
C([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:23][C@H:22](/[CH:24]=[CH:25]/[P:26](=[O:29])([OH:28])[OH:27])[C@@H:21]([OH:30])[C@H:20]1[OH:31])(=O)C1C=CC=CC=1.[NH4+].[OH-]>>[NH2:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:23][C@H:22](/[CH:24]=[CH:25]/[P:26](=[O:27])([OH:28])[OH:29])[C@@H:21]([OH:30])[C@H:20]1[OH:31]Participants
3
Procedure
Compound 24.3 (43 mg, 0.961 mmol) was treated with concentrated NH4OH (4.85 mL, 0.02 M) and stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was treated with 1% AcOH (2 mL). Reverse phase HPLC afforded compound 24.4 (23 mg, 70% yield) as a white solid: 1H NMR (D2O, 300 MHz) 8.21 (s, 1H), 8.11 (s, 1H), 6.41 (m, 1H), 5.97 (d, J=5.7 Hz, 1H), 5.84 (m, 1H), 4.66 (appt t, J=4.8 Hz, 1H), 4.53 (m, 1H), 4.22 (t, J=4.8 Hz, 1H); 31P NMR (D2O, 121.4 MHz) 9.4; MS (ESI) m/z 344 [M+H]+.