Tetrabutylammonium Fluoride → 596103-01-4

HRID 1268717Notes

Reaction equation

HRID 1268717 reaction equation
[CH3:1][NH:2][C:3]([C@@H:5]1[C@@H:9]([O:10][Si](C(C)(C)C)(C)C)[C@@H:8]([O:18][Si](C(C)(C)C)(C)C)[C@H:7]([N:26]2[CH:34]=[N:33][C:32]3[C:27]2=[N:28][C:29]([Cl:44])=[N:30][C:31]=3[NH:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([I:43])[CH:38]=2)[S:6]1)=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][NH:2][C:3]([C@@H:5]1[C@@H:9]([OH:10])[C@@H:8]([OH:18])[C@H:7]([N:26]2[CH:34]=[N:33][C:32]3[C:27]2=[N:28][C:29]([Cl:44])=[N:30][C:31]=3[NH:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([I:43])[CH:38]=2)[S:6]1)=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86601635HCID 86601635, compound

Product 1

HCID 11813713596103-01-4Yield 65.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

75 mg (0.09 mmol) of (2S,3S,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-tetrahydrothiophene-2-carboxylic acid methyl amide from the aforementioned Experimental Example 35 were dissolved in 5 mL of anhydrous tetrahydrofuran to which 0.25 mL (0.25 mmol, 1 mol tetrahydrofuran solution) of tetrabutylammonium fluoride was added. The reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was distilled under reduced pressure and the concentrate was purified by silica gel column chromatography using the eluant (dichloromethane:methanol=7:1) to obtain 33 mg (yield: 63%) of (2S,3S,4R,5R)-5-[2-chloro-6-(3-iodobenzylamino)purin-9-yl]-3,4-dihydroxytetrahydrothiophene-2-carboxylic acid methyl amide as white solids (see Table 3).

Workup

  1. additionwas added
  2. distillationThe reaction mixture was distilled under reduced pressure
  3. customthe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-680d96ea383346dba39d68be6d087e62
Source dataset
uspto-grants-2007_04
Patent number
US07199127B2

Reaction notes

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