Tributylvinyltin → HCID 14430336, compound

HRID 2050601Notes

Reaction equation

I[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH:21]([Sn](CCCC)(CCCC)CCCC)=[CH2:22]>CN(C=O)C.CC#N.CC#N.Cl[Pd]Cl>[CH:21]([C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11])=[CH2:22]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-iodoadenosine (1.585 g, 4.03 mmol) and bis(acetonitrile)palladium chloride (0.053 g, 0.20 mmol) in DMF (20 ml) was added vinyltributyltin (1.24 ml, 4.23 mmol), and the mixture stirred at 100° C. for 1 h. The reaction mixture was cooled and filtered. The solvent was evaporated and the residue was purified through silica gel with chloroform and 10% methanol/chloroform to give 1.099 g (92%) of 2-vinyladenosine: 1H NMR (Me2SO-d6) δ3.66 (m, 2H), 3.98 (m, 1H), 4.16 (m, 1H), 4.65 (m, 1H), 5.18 (d, 1H), 5.38-5.62 (m, 3H), 5.89 (d, 1H), 6.41 (dd, 1H), 6.59 (dd, 1H), 7.27 (br.s, 2H), 8.32 (s, 1H); UV (EtOH) λmax 293 nm, 271 nm, 265 nm.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered
customThe solvent was evaporated
customthe residue was purified through silica gel with chloroform and 10% methanol/chloroform

Sources & evidence

ORD record: ord-ebf87c1debc24c1b82a7b24bcc40fe8e
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05013829

Reaction notes

Loading…