Sodium Hydroxide → 3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

HRID 2386355Notes

Reaction equation

HRID 2386355 reaction equation
C([O:3][C:4](=[O:27])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[N:12]=2)[CH:6]=1)C.[OH-].[Na+]>CO>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][NH:17][C:13]2[N:12]=[C:11]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[C:4]([OH:27])=[O:3])[CH:16]=[CH:15][N:14]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 586036623-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid ethyl ester

Product 1

HCID 670445203-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 66 (2.4 g) was treated with 20 equivalents of sodium hydroxide in methanol. The mixture was heated at 50 C for 2 hours and the solvent removed by rotary evaporation. The residue was taken up in water and brought to pH 7 by addition of 1N HCl. The solvent was again removed by rotary evaporation. LC-MS showed the product had the expected M+H+ of 336. The crude product containing NaCl was used without purification in the next step.

Workup

  1. temperatureThe mixture was heated at 50 C for 2 hours
  2. customthe solvent removed by rotary evaporation
  3. additionbrought to pH 7 by addition of 1N HCl
  4. customThe solvent was again removed by rotary evaporation
  5. additionThe crude product containing NaCl
  6. customwas used without purification in the next step

Sources & evidence

ORD record
ord-12683939f821495c83ef286946dc7145
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

Loading…