Tetrahydrofuran → 3-Amino-6-(4-(3-hydroxypropyl)phenyl)-N-(pyridin-3-yl)pyrazine-2-carboxamide

HRID 217773Notes

Reaction equation

HRID 217773 reaction equation
[NH2:1][C:2]1[C:3]([C:25]([NH:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[O:26])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][O:17][Si](C(C)(C)C)(C)C)=[CH:10][CH:9]=2)=[CH:6][N:7]=1.C1COCC1.[OH-].[Na+]>O>[NH2:1][C:2]1[C:3]([C:25]([NH:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[O:26])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][OH:17])=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 666786503-Amino-6-(4-(3-(tert-butyldimethylsilyloxy)propyl)phenyl)-N-(pyridin-3-yl)-pyrazine-2-carboxamide

Product 1

HCID 666790683-Amino-6-(4-(3-hydroxypropyl)phenyl)-N-(pyridin-3-yl)pyrazine-2-carboxamideYield 91.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product of step (vi) (14.5 g, 31.3 mmol) was added to a plastic vessel and THF (150 mL) added. HF (30 mL) was added carefully to the solution and the solution stirred at room temperature for 3 hours. The mixture was poured to 600 mL of water and 5 N—NaOH added to basify the solution to pH=10-11. The solution was extracted with EtOAc and washed with water (×3). The combined EtOAc extract was dried over MgSO4, filtered and concentrated in vacuo, which afforded the subtitle compound (vii) as a yellow solid (10 g).

Workup

  1. additionHF (30 mL) was added carefully to the solution
  2. additionadded
  3. extractionThe solution was extracted with EtOAc
  4. washwashed with water (×3)
  5. extractionThe combined EtOAc extract
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo, which

Sources & evidence

ORD record
ord-dd204ced8ede470395b3fd2221d7c9c6
Source dataset
uspto-grants-2012_06
Patent number
US08198285B2

Reaction notes

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