Tetrabutylammonium Fluoride → HCID 86622806, compound

HRID 1641891Notes

Reaction equation

HRID 1641891 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:18][C:19]2[N:27]=[C:26]([Cl:28])[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[C@@H:29]2[CH2:33][C@H:32]([N:34]3[CH:38]=[C:37]([C:39](C4C=CC=CC=4)(C4C=CC=CC=4)[O:40][SiH2]C(C)(C)C)[CH:36]=[N:35]3)[C@@H:31]([OH:58])[C@H:30]2[OH:59])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:18][C:19]2[N:27]=[C:26]([Cl:28])[N:25]=[C:24]3[C:20]=2[N:21]=[CH:22][N:23]3[C@@H:29]2[CH2:33][C@H:32]([N:34]3[CH:38]=[C:37]([CH2:39][OH:40])[CH:36]=[N:35]3)[C@@H:31]([OH:58])[C@H:30]2[OH:59])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131729448HCID 131729448, compound

Product 1

HCID 86622806HCID 86622806, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1R,2S,3R,5S)-3-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-5-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pyrazol-1-yl]-cyclopentane-1,2-diol (step 1) (0.2 g, 0.24 mmol) is placed in a flask with THF (0.5 mL). Tetrabutylammonium fluoride (1M in THF, 0.26 mL, 0.26 mmol) is added and the reaction mixture is stirred at room temperature for 2 hours. The solvent is removed in vacuo and the title compound is obtained after purification by flash column chromatography (silica, dichloromethane/methanol 25:1). MS (ES+) m/e 592 (MH+).

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-3d2b1a279b534389b1e48cec6ca31ded
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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