Ethyl formate → HCID 20208695, compound

HRID 542483Notes

Reaction equation

HRID 542483 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][NH2:17])[N:8]=1.[CH:21](OCC)=[O:22]>CCO>[F:20][C:2]([F:1])([F:19])[CH2:3][N:4]=[C:5]([NH2:18])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][NH:17][CH:21]=[O:22])[N:8]=1

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 212987114-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine

Product 1

HCID 20208695HCID 20208695, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-(3-aminopropylthio)pyrimidine (0.3 g.), ethyl formate (5 ml.) and EtOH (2 ml.) was heated under reflux for 48 hours, 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, extracted with EtOAc and the extract dried and evaporated to dryness. The residue was recrystallised from EtOAc to give N-[3-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-ylthio)propyl]formamide (0.2 g.), m.p. 165°-166°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 hours
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in N aqueous HCl
  5. washthe solution washed with EtOAc
  6. extractionextracted with EtOAc
  7. customthe extract dried
  8. customevaporated to dryness
  9. customThe residue was recrystallised from EtOAc

Sources & evidence

ORD record
ord-0a80727e481342e6a933530f1da94679
Source dataset
uspto-grants-1987_04
Patent number
US04657908

Reaction notes

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