Sodium hydride → 2,6-Diamino-9-[2-O-(imidazol-1-yl)butyl-beta-D-ribofuranosyl]purine

HRID 1720554Notes

Reaction equation

HRID 1720554 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]2[OH:13])=[C:4]([NH2:20])[N:3]=1.[H-].[Na+].BrCCCC[C:28]1[NH:29][CH:30]=[CH:31][N:32]=1>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]2[O:13][CH2:11][CH2:12][CH2:14][CH2:16][N:29]2[CH:30]=[CH:31][N:32]=[CH:28]2)=[C:4]([NH2:20])[N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 722002-AminoadenosineHCID 54350134Bromobutylimidazole

Product 1

HCID 228747352,6-Diamino-9-[2-O-(imidazol-1-yl)butyl-beta-D-ribofuranosyl]purine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2,6-Diamino-(9-β-D-ribofuranosyl)purine (5.0 g) in DMF (400 ml) was treated with sodium hydride (0.78 g). After stirring an additional 30 min a further portion of sodium hydride (2.6 g) was added immediately followed by bromobutylimidazole (9.9 g) in DMF (25 ml). The reaction mixture was stirred overnight and quenched with H2O. The reaction mixture was filtered through celite and evaporated to yield an oily product. TLC showed a mixture of isomers.

Workup

  1. additionwas added immediately
  2. customquenched with H2O
  3. filtrationThe reaction mixture was filtered through celite
  4. customevaporated
  5. customto yield an oily product
  6. additiona mixture of isomers

Sources & evidence

ORD record
ord-f94050a9e2b746d388039d5a8221fde2
Source dataset
uspto-grants-1996_04
Patent number
US05506351

Reaction notes

Loading…