Acetic Acid → 2-(4-{[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-2-yl]amino}phenyl)acetic acid

HRID 3215Notes

Reaction equation

HRID 3215 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:30](=[O:31])[N:29]([CH3:32])[C:12]2[N:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27]C)=[O:26])=[CH:20][CH:19]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1.[OH-].[Na+].C(O)(=O)C>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:30](=[O:31])[N:29]([CH3:32])[C:12]2[N:13]=[C:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][CH:19]=3)[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 11619734{4-[6-(2,6-Dichlorophenyl)-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]phenyl}-acetic acid, methyl ester

Product 1

HCID 53279172-(4-{[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-2-yl]amino}phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A quantity of 0.065 g (0.14 mmol) of {4-[6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]phenyl}-acetic acid, methyl ester of Example 84 was dissolved in 25 mL of hot methanol with stirring. At the boiling point, 1 mL of 2N sodium hydroxide was added. After 1 hour reflux, the solution was concentrated to 5 mL volume (solid was out of solution). Water (10 mL) was added to give a complete solution. Glacial acetic acid (0.25 mL) was added to precipitate the solid free acid product. The solid was filtered, washed well with water, and dried; wt 0.060 g. Purification was accomplished by dissolution in 60 mL of 50% methanol/methylene chloride. Traces of solids were filtered, and the filtrate was concentrated with stirring to 2 mL volume. The separated solid was filtered and washed with 0.5 mL of methanol and ether; wt 0.050 g; mp 286°-290° C.

Workup

  1. temperatureAfter 1 hour reflux
  2. concentrationthe solution was concentrated to 5 mL volume (solid was out of solution)
  3. additionWater (10 mL) was added
  4. customto give a complete solution
  5. customto precipitate the solid free acid product
  6. filtrationThe solid was filtered
  7. washwashed well with water
  8. customdried
  9. customPurification
  10. dissolutionwas accomplished by dissolution in 60 mL of 50% methanol/methylene chloride
  11. filtrationTraces of solids were filtered
  12. concentrationthe filtrate was concentrated
  13. stirringwith stirring to 2 mL volume
  14. filtrationThe separated solid was filtered
  15. washwashed with 0.5 mL of methanol and ether

Sources & evidence

ORD record
ord-73007926fa184342830a1dbd65d16aa0
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

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