Sodium Hydroxide → 4-[(4-Pyrazin-2-yl-pyrimidin-2-ylamino)-methyl]-benzoic acid

HRID 852911

Reaction equation

HRID 852911 reaction equation
O.O.C[O:4][C:5](=[O:17])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([NH2:16])=[NH:15])=[CH:8][CH:7]=1.CN(/[CH:21]=[CH:22]/[C:23]([C:25]1[CH:30]=[N:29][CH:28]=[CH:27][N:26]=1)=O)C.C[O-].[Na+].[OH-].[Na+]>CO.O>[N:26]1[CH:27]=[CH:28][N:29]=[CH:30][C:25]=1[C:23]1[CH:22]=[CH:21][N:16]=[C:14]([NH:13][CH2:12][C:9]2[CH:10]=[CH:11][C:6]([C:5]([OH:4])=[O:17])=[CH:7][CH:8]=2)[N:15]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5825354(E)-3-(Dimethylamino)-1-(pyrazin-2-YL)prop-2-EN-1-oneHCID 10942334Sodium MethoxideHCID 1784979354-Guanidinomethyl-benzoic acid methyl ester dihydrate

Product 1

HCID 666221674-[(4-Pyrazin-2-yl-pyrimidin-2-ylamino)-methyl]-benzoic acidYield 87.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Procedure

A suspension of 24 (6.2 g, 25.4 mmol) and 23a (3.0 g, 16.9 mmol) in anhydrous methanol (40 mL) was stirred and heated to reflux for 10 min, then a solution of sodium methoxide 95% (3.65 g, 67.6 mmol) in methanol (40 mL) was slowly added. After refluxing for 24 h, 20 mL of 2.5N NaOH in water were added and the refluxing was maintained for additional 24 h. The mixture was allowed to cool to the room temperature methanol was removed under reduced pressure, 100 mL of water were added and the resultant mixture was extracted with AcOEt. The aqueous phase was separated and acidified to pH 5-6 with 2N HCl to form a precipitate which was collected by filtration, rinsed with water and dried to afford the desired carboxylic acid 25a (4.55 g, 14.8 mmol, 87%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 10 min
  3. temperatureAfter refluxing for 24 h
  4. temperaturethe refluxing was maintained for additional 24 h
  5. customwas removed under reduced pressure, 100 mL of water
  6. additionwere added
  7. extractionthe resultant mixture was extracted with AcOEt
  8. customThe aqueous phase was separated
  9. customto form a precipitate which
  10. filtrationwas collected by filtration
  11. washrinsed with water
  12. customdried

Sources & evidence

ORD record
ord-6fd3e27df8764876b3ae31b0ddb88e9c
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Linked notes

Loading…