Allyl bromide → 3'-O-Allyladenosine

HRID 565826Notes

Reaction equation

HRID 565826 reaction equation
[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[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].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[H-].[Na+].[CH2:36](Br)[CH:37]=[CH2:38]>CN(C=O)C>[CH2:38]([O:5][C@@H:4]1[C@@H:6]([CH2:7][OH:8])[O:9][C@@H:1]([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[C@@H:2]1[OH:3])[CH:37]=[CH2:36]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 14812Phosphorus oxide (P4O10)HCID 24758Sodium hydrideHCID 60961Adenosine

Product 1

HCID 110012923'-O-AllyladenosineYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Adenosine (20 g, 74.84 mmol) was dried over P2O5 under high vacuum at 40° C. for two days. It was then suspended in DMF under inert atmosphere. Sodium hydride (2.5 g, 74.84 mmol, 60% dispersion in mineral oil), stirred at room temperature for 10 minutes. Then allyl bromide (7.14 mL, 82.45 mmol) was added dropwise and the reaction mixture was stirred at room temperature overnight. DMF was removed under vacuum and residue was washed with ethyl acetate (100 mL). Ethyl acetate layer was decanted. Filtrate obtained contained product. It was then placed on a flash column and eluted with 10% MeOH in CH2Cl2 to get 109 (15.19 g, 66%). Rf 0.4, 0.4a ((10% MeOH in CH2Cl2)

Workup

  1. customDMF was removed under vacuum and residue
  2. washwas washed with ethyl acetate (100 mL)
  3. customEthyl acetate layer was decanted
  4. customFiltrate obtained
  5. washeluted with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-72e12616b76648e6a4f85c85b94f7002
Source dataset
uspto-grants-2001_01
Patent number
US06172209B2

Reaction notes

Loading…