Pyridine → 5'-Chloro-5'-deoxy-8-(methylamino)adenosine
Reaction equation
[Cl:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([NH2:13])[C:11]=3[N:10]=[C:9]2C)[C@H:5]([OH:19])[C@@H:4]1[OH:20].[N:21]1C=CC=C[CH:22]=1.O=S(Cl)Cl>CC#N>[Cl:1][CH2:2][C@H:3]1[O:7][C@@H:6]([N:8]2[C:17]3[N:16]=[CH:15][N:14]=[C:12]([NH2:13])[C:11]=3[N:10]=[C:9]2[NH:21][CH3:22])[C@H:5]([OH:19])[C@@H:4]1[OH:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound 3c was prepared by the same procedure as described for the preparation of 3a using 2c41 (2.9 g, 9.78 mmol), pyridine (1.54 g, 1.57 mL, 19.46 mmol), CH3CN (5 mL), and SOCl2 (5.82 g, 3.56 mL, 48.91 mmol): yield 1.95 g (63%); MS m/z 315 (M+H)+; 1HNMR (DMSO-d6) δ 7.91 (bs, 1H, H-2), 6.78 (q, 1H, 8CH3—NH), 6.50 (bs, 2H, 6-NH2), 5.70 (d, 1H, H-1′, J1′,2′=5.0 Hz), 5.41 (d, 1H, 2′-OH, J2′-2′OH=5.6 Hz), 5.32 (d, 1H, 3′-OH, J3′-3′OH=5.3 Hz), 5.18 (ddd, 1H, H-2′, J1′,2′=5.0 Hz, J2′,3′=5.4 Hz, J2′-2′OH=5.6 Hz), 4.33 (ddd, 1H, H-3′, J2′,3′=5.4 Hz, J3′,4′=4.4 Hz, J3′-3′OH=5.3 Hz), 3.91-4.02 (bm, 2H, H-4′,5′-CH2), 3.76-3.82 (m, 1H, 5′-CH2), 2.88 (d, 3H, 8NH—CH3, J=4.5 Hz).
Sources & evidence
- ORD record
- ord-713a56829e284bec998aa3b19929322b
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637485B2
Reaction notes
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