Propargyl bromide → HCID 86755938, compound

HRID 366840Notes

Reaction equation

HRID 366840 reaction equation
[CH2:1](Br)[C:2]#[CH:3].N12CCCN=C1CCCCC2.[C@@H:16]1([N:25]2[C:34]3[N:33]=[CH:32][N:31]=[C:29]([OH:30])[C:28]=3[N:27]=[CH:26]2)[O:24][C@H:21]([CH2:22][OH:23])[C@@H:19]([OH:20])[C@H:17]1[OH:18]>CC(N(C)C)=O.C(Cl)(Cl)Cl.CO>[CH2:1]([N:31]1[CH:32]=[N:33][C:34]2[N:25]([C@@H:16]3[O:24][C@H:21]([CH2:22][OH:23])[C@@H:19]([OH:20])[C@H:17]3[OH:18])[CH:26]=[N:27][C:28]=2[C:29]1=[O:30])[C:2]#[CH:3]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178521066(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-hydroxypurin-9-yl)oxolane-3,4-diol

Product 1

HCID 86755938HCID 86755938, compound

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21584188Chloroform methanolSolvent2×

Procedure

Propargyl bromide (11.8 ml, 105.9 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (20.62 ml, 135.2 mmol) were added to a suspension of inosine (27.56 g, 102.8 mmol) in dimethylacetamide (590 ml). The reaction mixture was stirred at room temperature overnight under argon, at which time TLC in chloroform/methanol (85:15) demonstrated disappearance of starting material. The reaction was terminated by addition to the suspension 3.5 L of ether/hexane (1:1) with storage at about -20 degrees C. overnight. While still chilled, solvent was decanted from the resulting gum, which was then dissolved in methanol and evaporated in vacuo (oil pump) onto silica gel. The product was isolated by silica gel chromatography using chloroform/methanol (95:5). The product was then characterized using mass spectrometry and proton NMR data. The mass spectrometer gave the following results: FABMS(glycerol), m/z 307 (MH+). The NMR data gave the following results: 1H-NMR (DMSO-d6): 8.50 (1H, s, H2); 8.39 (1H, s, H8); 5.87, 5.84 (1H, d, H1'); 5.51, 5.49 (1H, d, 2--OH); 5.23, 5.20 (1H, d, 3'--OH); 5.05 (1H, t, 5'--OH); 4.84, 4.83 (2H, d, CH2); 4.44 (1H, m, H2); 4.11, (1H, m, H3'), 3.92 (1H, m, H4'); 3.62 (1H, m, H5'); 3.57 (1H, m, H5'); 3.41 (1H, t, CH). Characterization with mass spec. and NMR yielded data consistent with the structure of 1-propargylinosine.

Workup

  1. customThe reaction was terminated by addition to the suspension 3.5 L of ether/hexane (1:1) with storage at about -20 degrees C
  2. customovernight
  3. temperatureWhile still chilled
  4. customsolvent was decanted from the resulting gum, which
  5. dissolutionwas then dissolved in methanol
  6. customevaporated in vacuo (oil pump) onto silica gel
  7. customThe product was isolated by silica gel chromatography
  8. customThe mass spectrometer gave the
  9. customfollowing results
  10. customThe NMR data gave the
  11. customfollowing results

Sources & evidence

ORD record
ord-4d61136f99cc4da9b6a74c04618430b4
Source dataset
uspto-grants-2000_10
Patent number
US06130324

Reaction notes

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