Potassium Hydroxide → HCID 178512204, compound

HRID 1462343Notes

Reaction equation

HRID 1462343 reaction equation
[F:1][C:2]([F:35])([F:34])[CH2:3][N:4]=[C:5]([NH2:33])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:32])[CH2:20][NH:21][C:22](OCC2C=CC=CC=2)=[O:23])[N:8]=1.[OH-].[K+].[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]\[C:41]([OH:43])=[O:42]>CCO>[C:38]([OH:45])(=[O:44])/[CH:39]=[CH:40]\[C:41]([OH:43])=[O:42].[OH:23][C:22]1[N:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:9]2[N:8]=[C:7]([NH:6][C:5]([NH2:33])=[N:4][CH2:3][C:2]([F:35])([F:34])[F:1])[CH:12]=[CH:11][N:10]=2)[C:19]([OH:32])=[CH:20][N:21]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 444266Maleic AcidHCID 202469454-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[5-(2-benzyloxycarbonylaminoacetylamino)pentyl]pyrimidine

Product 1

HCID 178512204HCID 178512204, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[5-(2-benzyloxycarbonylaminoacetylamino)pentyl]pyrimidine (0.2 g.) was added 13 ml. of a solution of potassium hydroxide (0.096 g.) in EtOH (50 ml.), and the mixture was heated under reflux for 35 minutes. The mixture was evaporated in vacuo, a few drops of aqueous HOAc was added to the residue, followed by sodium bicarbonate solution until pH 7 was obtained. The mixture was extracted with EtOAc, the extract dried and evaporated to give a pale yellow solid. This was dissolved in a small volume of hot EtOH and a solution of maleic acid (0.05 g.) in EtOH (0.5 ml.) added. There was obtained 2,4-dihydroxy-3-(5-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yl]pentyl)imidazole maleate (0.13 g.), m.p. 172°-174°.

Workup

  1. temperatureunder reflux for 35 minutes
  2. customThe mixture was evaporated in vacuo, a few drops of aqueous HOAc
  3. additionwas added to the residue
  4. customwas obtained
  5. extractionThe mixture was extracted with EtOAc
  6. customthe extract dried
  7. customevaporated
  8. customto give a pale yellow solid

Sources & evidence

ORD record
ord-4d137265eff3498cb7e1cda34792bfda
Source dataset
uspto-grants-1984_07
Patent number
US04460584

Reaction notes

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