Imidazole → HCID 178455235, compound

HRID 2209756Notes

Reaction equation

[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14](N)[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].N1C=CN=C1.[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26].CN(C)C=[O:36]>>[Si:29]([O:8][CH2:7][C@H:6]1[O:9][C@@H:1]([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([OH:36])[C:13]=3[N:12]=[CH:11]2)[C@H:2]([OH:3])[C@@H:4]1[OH:5])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30]

Participants

Reactant 4

HCID 795Imidazole

HCID 6228Dimethylformamide

HCID 28928tert-Butyldimethylsilyl chloride

HCID 60961Adenosine

Product 1

HCID 178455235HCID 178455235, compoundYield 76.7%

Procedure

A mixture of inosine 13 (15.0 g, 56 mmol) (dried by coevaporation with 70 ml of dimethylformamide (DMF)), imidazole (9.52 g, 140 mmol) and tertbutyldimethylsilyl chloride (10.1 g, 67 mmol) in DMF (125 ml) was stirred at room temperature for 12 h. The solvent was removed in vacuo and the residue was purified chromatographically using CHCl3 -methanol (15:2) as the eluent to obtain 16.4 g (76.7%) of 18: mp softening at 220° C., melting at 229°-231° C. (CHCl3 -diethyl ether); 1H NMR (DMSO-d6) δ 0.0 (6H, s, (CH3)2Si), 0.82 (9H, s, (CH3)3CSi), 3.52-4.00 (3H, m, 4' and 5'-H), 4.10 (1H, t, J=4.8 Hz, 2'(3')-H), 4.41 (1H, t, J=4.8 HZ, 3'(2')-H), 5.83 (1H, d, J=5.3 HZ, 1'-H), 8.00 (1H, s, 8-H), 8.18 (1H, s, 2-H).

Workup

customThe solvent was removed in vacuo
customthe residue was purified chromatographically using CHCl3 -methanol (15:2) as the eluent

Sources & evidence

ORD record: ord-fff01267cf6b43558ae75a40817ff165
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05455339

Reaction notes

Loading…