Ethanol → N-[3-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimidin-2-yl-thio)propyl]-2-furamide

HRID 542479Notes

Reaction equation

HRID 542479 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[F:9][C:10]([F:28])([F:27])[CH2:11][N:12]=[C:13]([NH2:26])[NH:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH2:22][CH2:23][CH2:24][NH2:25])[N:16]=1.CCO>C(N(CC)CC)C>[F:28][C:10]([F:9])([F:27])[CH2:11][N:12]=[C:13]([NH2:26])[NH:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([S:21][CH2:22][CH2:23][CH2:24][NH:25][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[O:7])[N:16]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 682422-Furancarbonyl chlorideHCID 212987114-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine

Product 1

HCID 20208710N-[3-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimidin-2-yl-thio)propyl]-2-furamideYield 74.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-Furoyl chloride (145 mg.) was added to a mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine (308 mg.), EtOH (10 ml.) and triethylamine (0.5 ml.), the mixture left at room temperature for 2 hours and then evaporated to dryness. The residue was dissolved in N aqueous HCl and the solution washed with EtOAc. The aqueous phase was basified with 10N aqueous NaOH and then extracted with EtOAc, and the extract was dried amd evaporated to dryness. The residue was recrystallised from EtOAc to give N-[3-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimidin-2-yl-thio)propyl]-2-furamide (300 mg.), m.p. 127°-129°.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in N aqueous HCl
  3. washthe solution washed with EtOAc
  4. extractionextracted with EtOAc
  5. customthe extract was dried amd
  6. customevaporated to dryness
  7. customThe residue was recrystallised from EtOAc

Sources & evidence

ORD record
ord-4731daa5634944d893ce0a90f77c3574
Source dataset
uspto-grants-1987_04
Patent number
US04657908

Reaction notes

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