Potassium Hydroxide → {5-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

HRID 1642093Notes

Reaction equation

HRID 1642093 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[NH:7][CH:8]=[CH:9][C:2]=12.[C:10]([O:14][C:15](=[O:34])[N:16]([C:26]1[CH:31]=[CH:30][C:29]([CH:32]=[O:33])=[CH:28][N:27]=1)[CH2:17][C:18]1[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)([CH3:13])([CH3:12])[CH3:11].[OH-].[K+]>CO>[C:10]([O:14][C:15](=[O:34])[N:16]([C:26]1[CH:31]=[CH:30][C:29]([CH:32]([OH:33])[C:9]2[C:2]3[C:3](=[N:4][CH:5]=[CH:6][N:1]=3)[NH:7][CH:8]=2)=[CH:28][N:27]=1)[CH2:17][C:18]1[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 53708035H-Pyrrolo[2,3-b]pyrazineHCID 57619225(5-Formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

Product 1

HCID 58001690{5-[hydroxy-(5H-pyrrolo[2,3-b]pyrazin-7-yl)-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl esterYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5H-Pyrrolo[2,3-b]pyrazine (3, 0.150 g, 1.26 mmol) in 2.2 mL of methanol, (5-formyl-pyridin-2-yl)-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (6, 0.52 g, 1.5 mmol) and potassium hydroxide (0.230 g, 4.10 mmol) were added. The reaction was allowed to stir at room temperature overnight, then concentrated and poured into saturated sodium bicarbonate, and extracted with ethyl acetate. The organic portion was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum and purified by silica gel chromatography to provide the desired compound (7, 0.22 g, 38%).

Workup

  1. concentrationconcentrated
  2. additionpoured into saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. washThe organic portion was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum
  8. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b5fbcbc5ff984b0a90a7791ef3ab05b7
Source dataset
uspto-grants-2012_02
Patent number
US08119637B2

Reaction notes

Loading…