Potassium Hydroxide → HCID 135528966, compound

HRID 1936638Notes

Reaction equation

HRID 1936638 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([O:21]CC)=[O:20])[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:24]1[NH:25][C:26](=[O:37])[C:27]2[N:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH2:35][CH3:36])[C:28]=2[N:29]=1)[CH3:2].[OH-].[K+]>C(O)C>[C:19]([CH:16]1[CH2:15][CH2:14][N:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:24]3[NH:25][C:26](=[O:37])[C:27]4[N:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH2:35][CH3:36])[C:28]=4[N:29]=3)[CH:6]=2)(=[O:12])=[O:11])[CH2:18][CH2:17]1)([OH:21])=[O:20]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 135430966HCID 135430966, compound

Product 1

HCID 135528966HCID 135528966, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[2-ethoxy-5-(4-ethoxycarbonylpiperidinosulphonyl)phenyl]-8-n-propylpyrido[3,2-d]pyrimidin-4(3H)-one (Example 4; 0.55 g, 0.001 mol), potassium hydroxide (0.146 g, 0.0026 mol) and ethanol (35 ml) was stirred under reflux for 5 hours, then allowed to cool. The solvent was evaporated under vacuum, and the residue chromatographed twice on ion-exchange resin (Bio-rad AG50W-X8 H+, 27.5 g) using a pyridine in water elution gradient (2-50% pyridine). Crystallization of the product from aqueous ethanol gave the title compound as a colourless solid (0.09 g, 8%), m.p. 262-264° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureto cool
  3. customThe solvent was evaporated under vacuum
  4. customthe residue chromatographed twice on ion-exchange resin (Bio-rad AG50W-X8 H+, 27.5 g)
  5. washa pyridine in water elution gradient (2-50% pyridine)
  6. customCrystallization of the product from aqueous ethanol

Sources & evidence

ORD record
ord-62b16bd21c8540f0a3a391054266ce66
Source dataset
uspto-grants-2002_05
Patent number
US06391885B1

Reaction notes

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