Lithium Hydroxide → 4-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[3-(1,3-oxazol-5-yl)phenyl]-2-pyrimidinamine

HRID 1157564Notes

Reaction equation

HRID 1157564 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]5[O:38][CH:37]=[N:36][CH:35]=5)[CH:29]=4)[N:22]=3)=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)[CH:7]=1)=O.[Li+].[OH-].C1COCC1>O>[NH2:5][C:6]1[CH:7]=[C:8]([C:12]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]5[O:38][CH:37]=[N:36][CH:35]=5)[CH:29]=4)[N:22]=3)=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 577372422,2,2-Trifluoro-N-{3-[3-(2-{[3-(1,3-oxazol-5-yl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}acetamide

Product 1

HCID 577371674-[2-(3-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[3-(1,3-oxazol-5-yl)phenyl]-2-pyrimidinamineYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,2,2-trifluoro-N-{3-[3-(2-{[3-(1,3-oxazol-5-yl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}acetamide (0.89 g, 0.002 mols) and 1M LiOH (8.22 mL, 0.008 mols) in 10:1 THF:water (20 mL) was heated at 60° C. for 5 h. The reaction was washed with brine (25 mL), organic layer separated, aqueous layer extracted with EtOAc (25 mL), organic layers combined, filtered through a cotton plug, and solvent removed by rotary evaporation. The crude product was purified by column chromatography (5%-75% EtOAc in hexanes then 100% EtOAc) to provide the aniline (0.70 g, 96%) as a pale yellow foam. ES-LC/MS m/z=446 [M+H]+.

Workup

  1. washThe reaction was washed with brine (25 mL), organic layer
  2. customseparated
  3. extractionaqueous layer extracted with EtOAc (25 mL), organic layers
  4. filtrationfiltered through a cotton plug, and solvent
  5. customremoved by rotary evaporation
  6. customThe crude product was purified by column chromatography (5%-75% EtOAc in hexanes

Sources & evidence

ORD record
ord-1c35ba18e7f449baaeafcab7f63f753a
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

Loading…