HCID 86038790, compound → HCID 86038792, compound

HRID 659996Notes

Reaction equation

HRID 659996 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[C:15]([Cl:17])[N:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1>C1COCC1.[Li+].[OH-].O>[Cl:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:18])=[O:2])=[CH:9][CH:8]=2)[CH:16]=1

Participants

5

Reactant 1

HCID 86038790HCID 86038790, compound

Product 1

HCID 86038792HCID 86038792, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(6-Chloro-pyrimidin-4-yl-amino)-benzoic acid methyl ester, (0.1 g, 0.38 mmol) in THF (3 mL), LiOH×H2O (0.017 g, 0.42 mmol) dissolved in H2O (1 mL) was added and the mixture stirred at room temperature for 18 h. The reaction mixture was then diluted with H2O (5 mL) and extracted with EtOAc (2×). The water layer was acidified (2.5M HCl) and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4) and the solvent evaporated under reduced pressure to afford 4-(6-Chloro-pyrimidin-4-yl-amino)-benzoic acid, as a pale yellow solid.

Workup

  1. additionwas added
  2. extractionextracted with EtOAc (2×)
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-c00d3b508cdc475eb803f2ea1b98ee8f
Source dataset
uspto-grants-2011_12
Patent number
US08084457B2

Reaction notes

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