Anthranilic Acid → 2-[(2-Methylamino-pyrimidin-4-ylmethyl)-amino]-benzoic acid

HRID 969695Notes

Reaction equation

HRID 969695 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][NH:12][C:13]1[N:18]=[C:17]([CH:19]=O)[CH:16]=[CH:15][N:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH3:11][NH:12][C:13]1[N:18]=[C:17]([CH2:19][NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])[CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 6101p-Toluenesulfonic acidHCID 4311764Sodium borohydrideHCID 220025312-(Methylamino)pyrimidine-4-carbaldehyde

Product 1

HCID 695125122-[(2-Methylamino-pyrimidin-4-ylmethyl)-amino]-benzoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of anthranilic acid (0.55 g, 4.0 mmol), 2-methylamino-pyrimidine-4-carbaldehyde (Step B, 0.72 g, 5.2 mmol), and p-toluenesulfonic acid mohohydrate (0.025 g, 0.13 mmol) in 20 mL of anhydrous toluene was stirred at reflux for 1 h, and cooled to RT. NaBH4 (0.41 g, 10.8 mmol) was added, and the mixture was stirred at RT for 30 min. The mixture was quenched with MeOH, the volatiles were removed under reduced pressure, and the residue was taken up in water. AcOH was added to bring the pH to 4 and the mixture was extracted with EtOAc. The combined organic portions were washed with brine, dried over MgSO4, filtered, condensed, and the residue was purified by flash column chromatography to give the titled compound. MS (ES+): 259.0 (M+H)+. Calc'd for C13H14N4O2-258.28

Workup

  1. temperatureat reflux for 1 h
  2. stirringthe mixture was stirred at RT for 30 min
  3. customThe mixture was quenched with MeOH
  4. customthe volatiles were removed under reduced pressure
  5. additionAcOH was added
  6. extractionthe mixture was extracted with EtOAc
  7. washThe combined organic portions were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customcondensed
  11. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-b7f62077799342e6be111383539a4bee
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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