Ethyl formate → HCID 20208695, compound

HRID 2413194Notes

Reaction equation

HRID 2413194 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 as basified with 10 N 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-d0dda318e0c7489fa7bb60cd2782c00c
Source dataset
uspto-grants-1985_01
Patent number
US04496571

Reaction notes

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