Potassium Hydroxide → 2-{6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-2-oxo-acetamide

HRID 886558Notes

Reaction equation

HRID 886558 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[N:23]=[CH:22][N:21]=[C:20]([C:24](=[O:30])[C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:19]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[N:23]=[CH:22][N:21]=[C:20]([C:24](=[O:30])[C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:19]=3)[CH:16]=2)[NH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 598250612-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-2-oxo-acetamide

Product 1

HCID 598250052-{6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-2-oxo-acetamideYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{6-[3-(2-Methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-2-oxo-acetamide (100 mg, 0.179 mmole) in methanol (3.6 mL) was cooled to 0° C. in an ice bath. Potassium hydroxide (aqueous 50% w/v, 0.06 mL) was added, the solution removed from the ice bath, maintained at ambient temperature for 15 hrs, and quenched with acetic acid (0.06 mL). The resulting solution was concentrated to remove all volatile organics, dissolved in ethyl acetate (10 mL), washed with sodium bicarbonate (5 mL), then with water (5 mL), then with brine (5 mL), and dried over magnesium sulfate. The solution was filtered and concentrated to dryness to afford 2-{6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyrimidin-4-yl}-N,N-dimethyl-2-oxo-acetamide (63 mg, 72%) as a yellow solid which was used without further purification. MS: m/z 402.2 (M+H+).

Workup

  1. customthe solution removed from the ice bath
  2. customquenched with acetic acid (0.06 mL)
  3. concentrationThe resulting solution was concentrated
  4. customto remove all volatile organics,
  5. dissolutiondissolved in ethyl acetate (10 mL)
  6. washwashed with sodium bicarbonate (5 mL)
  7. dry with materialwith water (5 mL), then with brine (5 mL), and dried over magnesium sulfate
  8. filtrationThe solution was filtered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-05bd48799ecf45d3939e5dcc47579b8a
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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