Tetrabutylammonium Fluoride → 3-Amino-6-(4-(2-hydroxyethyl)phenyl)-N-(pyridin-3-yl)pyrazine-2-carboxamide

HRID 217789Notes

Reaction equation

HRID 217789 reaction equation
[NH2:1][C:2]1[C:3]([C:24]([NH:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:25])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][O:16][Si](C(C)(C)C)(C)C)=[CH:10][CH:9]=2)=[CH:6][N:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:1][C:2]1[C:3]([C:24]([NH:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:25])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66678104HCID 66678104, compound

Product 1

HCID 666787633-Amino-6-(4-(2-hydroxyethyl)phenyl)-N-(pyridin-3-yl)pyrazine-2-carboxamideYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of step (ii) (4.1 g, 9.13 mmol) and tetrabutyl ammonium fluoride (4.8 g, 18.3 mmol) in THF (150 mL) was stirred at room temperature overnight. The mixture was concentrated in vacuo and the residue extracted with dichloromethane and washed with water. The combined organic layers were dried overanhydrous sodium sulphate, filtered and concentrated in vacuo to obtain the subtitle compounds (2.5 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionthe residue extracted with dichloromethane
  3. washwashed with water
  4. dry with materialThe combined organic layers were dried overanhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85b71f46ca01460193d28e9a8f3b3116
Source dataset
uspto-grants-2012_06
Patent number
US08198285B2

Reaction notes

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