Imidazole → HCID 131726595, compound

HRID 915882Notes

Reaction equation

HRID 915882 reaction equation
[NH2:1][C:2]1[C:3]2[C:4]3[C:5](=[CH:13][N:14]([C@@H:16]4[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@@:17]4([CH3:25])[OH:18])[N:15]=2)[CH:6]=[CH:7][C:8]=3[C:9](=[O:12])[NH:10][N:11]=1.[Si:26](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].N1C=CN=C1>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:4]3[C:5](=[CH:13][N:14]([C@@H:16]4[O:22][C@H:21]([CH2:23][O:24][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C@@H:19]([OH:20])[C@@:17]4([CH3:25])[OH:18])[N:15]=2)[CH:6]=[CH:7][C:8]=3[C:9](=[O:12])[NH:10][N:11]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86612909HCID 86612909, compound

Product 1

HCID 131726595HCID 131726595, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-2-(2-C-methyl-β-D-ribofuranosyl)-2,6-dihydro-7H-2,3,5,6-tetraazabenzo[cd]azulene-7-one (65 mg, 0.19 mmol) in DMF, tert-butyldimethylsilyl chloride (70 mg, 0.45 mmol) and imidazole (61 mg, 0.90 mmol) was stirred overnight at room temperature and then concentrated in vacuo. The oily residue was dissolved in CH2Cl2 (20 mL), washed with aq. HCl (0.1 N), sat.aq. NaHCO3, water, brine and dried (Na2SO4). The evaporated residue was purified on silica gel with hexanes/EtOAc (1/1)+0.5% Et3N and EtOAc+0.5% Et3N to yield the target compound 16.1 as colorless oil (38 mg, 44%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe oily residue was dissolved in CH2Cl2 (20 mL)
  3. washwashed with aq. HCl (0.1 N)
  4. dry with materialNaHCO3, water, brine and dried (Na2SO4)
  5. customThe evaporated residue was purified on silica gel with hexanes/EtOAc (1/1)+0.5% Et3N and EtOAc+0.5% Et3N

Sources & evidence

ORD record
ord-c60191a6018c4f4394ae3ca42b82a012
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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