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

HRID 341925

Reaction equation

HRID 341925 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-f2c8e7db6c7e46d09235f2aea90c43b1
Source dataset
uspto-grants-1999_01
Patent number
US05856466

Linked notes

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