N,N-Diethylethylenediamine → HCID 178464061, compound

HRID 34794Notes

Reaction equation

HRID 34794 reaction equation
[F:1][C:2]([F:26])([F:25])[CH2:3][N:4]=[C:5]([NH2:24])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[N:21][C:22]#[N:23])SC)[N:8]=1.[CH2:27]([N:29]([CH2:33][CH3:34])[CH2:30][CH2:31][NH2:32])[CH3:28]>CO>[F:1][C:2]([F:26])([F:25])[CH2:3][N:4]=[C:5]([NH2:24])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:32][CH2:31][CH2:30][N:29]([CH2:33][CH3:34])[CH2:27][CH3:28])=[N:21][C:22]#[N:23])[N:8]=1

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 178503922HCID 178503922, compound

Product 1

HCID 178464061HCID 178464061, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[3-(3-cyano-2-methylisothioureido)propylthio]pyrimidine (0.2 g.), N,N-diethylethylenediamine (0.5 ml.) and methanol (2 ml.) was heated under reflux for 24 hours and then evaporated to dryness. Water was added to the residue, the mixture extracted with ethyl acetate and the ethyl acetate extract dried and evaporated to dryness. The residue was purified by preparative thin layer chromatography using ethyl acetate/methanol/ammonia 6:1:0.5 v/v/v as developing solvent to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[3-(2-cyano-3-[2-diethylaminoethyl]guanidino)propylthio]pyrimidine (0.08 g.), characterised as the bis hydrogen maleate, m.p. 76°-80° after recrystallisation from acetone.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. customevaporated to dryness
  4. additionWater was added to the residue
  5. extractionthe mixture extracted with ethyl acetate
  6. extractionthe ethyl acetate extract
  7. customdried
  8. customevaporated to dryness
  9. customThe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-1966c4121bcf441c91402c29969d99fc
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Reaction notes

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