Sodium Hydroxide → 2-aminopyrido[2,3-d]pyrimidin-7(8H)-one 72

HRID 3218Notes

Reaction equation

HRID 3218 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[C:11]1[C:35](=[O:36])[N:34]([CH3:37])[C:14]2[N:15]=[C:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])=[CH:22][CH:21]=3)[N:17]=[CH:18][C:13]=2[CH:12]=1>C(O)(=O)C>[Cl:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[C:5]=1[C:11]1[C:35](=[O:36])[N:34]([CH3:37])[C:14]2[N:15]=[C:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:22][CH:21]=3)[N:17]=[CH:18][C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53279032-aminopyrido[2,3-d]pyrimidin-7(8H)-one 57

Product 1

HCID 53279182-aminopyrido[2,3-d]pyrimidin-7(8H)-one 72Yield 34.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A volume of 5 mL of 2N sodium hydroxide was added to a hot stirred solution of 0.170 g (0.33 mmol) of 4-[4-{6-(2,6-dichlorophenyl)-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-phenyl}-butyric acid, ethyl ester of Example 91. The solution was maintained at reflux for 1 hour. Glacial acetic acid (1 mL) was added, and the reaction solution was evaporated to ca. 25 mL volume. Water (50 mL) was added to precipitate a solid. The mixture was filtered, and the cake was washed well with water and dried; wt 0.130 g. Hydrolysis did not go to completion under these conditions. The product was purified to remove starting ester by silica gel chromatography eluting with 1:20 methanol:chloroform to obtain 55 mg of pure acid; mp 169°-171° C.

Workup

  1. temperatureThe solution was maintained
  2. temperatureat reflux for 1 hour
  3. customthe reaction solution was evaporated to ca. 25 mL volume
  4. additionWater (50 mL) was added
  5. customto precipitate a solid
  6. filtrationThe mixture was filtered
  7. washthe cake was washed well with water
  8. customdried
  9. customHydrolysis
  10. customThe product was purified
  11. customto remove
  12. washeluting with 1:20 methanol

Sources & evidence

ORD record
ord-a983572781e049c5930f6eb5910fc562
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Reaction notes

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