Potassium Fluoride → 1-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(Pyrimidin-4-yl)urea

HRID 1807755Notes

Reaction equation

HRID 1807755 reaction equation
[Si]([O:8][C:9]([C:18]1[CH:49]=[CH:48][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][N:26]([C:29]([C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38]([NH:40][C:41]4[CH:46]=[CH:45][N:44]=[CH:43][N:42]=4)=[O:39])=[C:33]([F:47])[CH:32]=3)=[O:30])[CH2:25][CH2:24]2)=[CH:20][CH:19]=1)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])(C(C)(C)C)(C)C.[F-].[K+]>O1CCCC1>[F:47][C:33]1[CH:32]=[C:31]([C:29]([N:26]2[CH2:27][CH2:28][N:23]([CH2:22][C:21]3[CH:20]=[CH:19][C:18]([C:9]([OH:8])([C:10]([F:13])([F:11])[F:12])[C:14]([F:15])([F:17])[F:16])=[CH:49][CH:48]=3)[CH2:24][CH2:25]2)=[O:30])[CH:36]=[CH:35][C:34]=1[NH:37][C:38]([NH:40][C:41]1[CH:46]=[CH:45][N:44]=[CH:43][N:42]=1)=[O:39]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 866385631-(4-(4-(4-(2-(Tert-butyldimethylsilyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)benzyl)-piperazine-1-carbonyl)-2-fluorophenyl)-3-(pyrimidin-4-yl)urea

Product 1

HCID 445123941-(2-Fluoro-4-(4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperazine-1-carbonyl)phenyl)-3-(Pyrimidin-4-yl)ureaYield 15.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(4-(4-(4-(2-(tert-butyldimethylsilyloxy)-1,1,1,3,3,3-hexafluoropropan-2-yl)benzyl)-piperazine-1-carbonyl)-2-fluorophenyl)-3-(pyrimidin-4-yl)urea (0.088 mmol, 0.0627 g) and potassium fluoride (50% on celite) (0.877 mmol, 0.102 g) were combined and heated to reflux in tetrahydrofuran (5 mL) overnight. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The resulting residue was purified by silica column chromatography (eluant dichloromethane/methanol 0% to 5%) to afford the title compound (8 mg). MS (ESI) m/z 601.3 [M+H]+

Workup

  1. temperatureheated
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe resulting residue was purified by silica column chromatography (eluant dichloromethane/methanol 0% to 5%)

Sources & evidence

ORD record
ord-e789497be40c4fd983a34b845bcb9d8f
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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