Pyridine, hydrofluoride (1:1) → Sonedenoson

HRID 1392015Notes

Reaction equation

HRID 1392015 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[N:12]=[C:13]([NH2:50])[C:14]3[N:15]=[CH:16][N:17]([C:48]=3[N:49]=2)[C@@H:18]2[O:47][C@H:37]([CH2:38][O:39][Si](C(C)(C)C)(C)C)[C@@H:28]([O:29][Si](C(C)(C)C)(C)C)[C@H:19]2[O:20][Si](C(C)(C)C)(C)C)=[CH:4][CH:3]=1.N1C=CC=CC=1.F>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][C:11]2[N:12]=[C:13]([NH2:50])[C:14]3[N:15]=[CH:16][N:17]([C:48]=3[N:49]=2)[C@@H:18]2[O:47][C@H:37]([CH2:38][OH:39])[C@@H:28]([OH:29])[C@H:19]2[OH:20])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 156063272-[2-(4-Chlorophenyl)ethoxy]-2',3',5'-tri-o-(tert-butyldimethylsilyl)-adenosine

Product 1

HCID 9910098SonedenosonYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-[2-(4-chlorophenyl)ethoxy]-2′,3′,5′-tri-O-(TERT-butyldimethylsilyl)-adenosine (Example 1, 500 mg, 0.654 mmol) in 7 mL of anhydrous methanol flushed with nitrogen was added 323 mg (5 equiv.) of hydrogen fluoride-pyridine. The reaction was heated to 50° C. for 18 hours. Upon disappearance of the starting material as indicated by LC analysis, the reaction was allowed to cool to room temperature, which resulted in precipitation of a white solid. This was collected by filtration, rinsed with 3 mL of methanol and dried to obtain 138 mg (50%) of the desired product as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. customwhich resulted in precipitation of a white solid
  3. filtrationThis was collected by filtration
  4. washrinsed with 3 mL of methanol
  5. customdried

Sources & evidence

ORD record
ord-af8f17c6d2cf4e3f80426d26103f6bb5
Source dataset
uspto-grants-2008_03
Patent number
US07342003B2

Reaction notes

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