Tetrabutylammonium Fluoride → HCID 59975334, compound

HRID 2268383Notes

Reaction equation

HRID 2268383 reaction equation
[Si]([O:8][C@@H:9]1[C@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@@H:12]([CH2:22][O:23][CH3:24])[O:11][C@H:10]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][C:28]([CH2:49][N:50]([CH:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1)[CH3:51])=[N:29][C:30]=2[NH:34][CH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:52]1([N:50]([CH2:49][C:28]2[N:27]=[C:26]3[C:31]([N:32]=[CH:33][N:25]3[C@H:10]3[C@H:9]([OH:8])[C@H:13]([OH:14])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11]3)=[C:30]([NH:34][CH2:35][CH:36]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:29]=2)[CH3:51])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69534077HCID 69534077, compound

Product 1

HCID 59975334HCID 59975334, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[cyclohexyl(methyl)amino]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine (133 mg, 0.16 mmol) (preparation 35) was dissolved in stirred tetrahydrofuran (1 ml) and a 1 molar solution of tetra-n-butylammonium fluoride in tetrahydrofuran (1 ml, 1 mmol) was added. The reaction mixture was stirred for 1 hr, then the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5) to give the title compound (83 mg) as a foam. MS: 587 (MH+).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5)

Sources & evidence

ORD record
ord-b863000810174cbc847052ce22d9e277
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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