Hydrochloric Acid → 2,4-Dihydroxy-1-(5-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yl]pentyl)imidazole maleate

HRID 1462345Notes

Reaction equation

HRID 1462345 reaction equation
[O-:1][C:2]#N.[K+].[F:5][C:6]([F:28])([F:27])[CH2:7][N:8]=[C:9]([NH2:26])[NH:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][CH2:23][C:24]#[N:25])[N:12]=1.Cl.[C:30](=[O:33])([O-])[O-:31].[Na+].[Na+].[OH2:36]>CC(O)=O>[C:2]([OH:1])(=[O:36])/[CH:23]=[CH:24]\[C:30]([OH:31])=[O:33].[OH:1][C:2]1[N:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:13]2[N:12]=[C:11]([NH:10][C:9]([NH2:26])=[N:8][CH2:7][C:6]([F:5])([F:27])[F:28])[CH:16]=[CH:15][N:14]=2)[CH:23]=[C:24]([OH:31])[N:25]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 11378442Potassium cyanateHCID 202469524-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[5-cyanomethylaminopentyl]pyrimidine

Product 1

HCID 1785122032,4-Dihydroxy-1-(5-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yl]pentyl)imidazole maleate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Potassium cyanate (0.055 g.) was added in portions to a solution of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[5-cyanomethylaminopentyl]pyrimidine (0.02 g.) in 80% v/v aqueous HOAc (2 ml.) at 0° and the mixture stirred for 1 hour, then heated at 60°-70° for 20 minutes. Concentrated aqueous hydrochloric acid (1 ml.) and water (0.6 ml.) were added and the mixture was heated on a steam bath for 30 minutes. On cooling, saturated sodium carbonate solution was added until the pH was approximately 7. The mixture was extracted with EtOAc, the extract dried (MgSO4) and evaporated. The residue was dissolved in EtOH (4 ml.) and a solution of maleic acid (0.065 g.) in EtOH (0.5 ml.) added. On standing there was obtained 2,4-dihydroxy-1-(5-[4-(2-[2,2,2-trifluoroethyl]guanidino)pyrimid-2-yl]pentyl)imidazole maleate (0.2 g.), m.p. 183°-185°.

Workup

  1. temperatureheated at 60°-70° for 20 minutes
  2. temperaturethe mixture was heated on a steam bath for 30 minutes
  3. temperatureOn cooling
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialthe extract dried (MgSO4)
  6. customevaporated
  7. dissolutionThe residue was dissolved in EtOH (4 ml.)
  8. additiona solution of maleic acid (0.065 g.) in EtOH (0.5 ml.) added

Sources & evidence

ORD record
ord-1875b7c52c784565adc6e476daf44b80
Source dataset
uspto-grants-1984_07
Patent number
US04460584

Reaction notes

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