N,N-Diethylethylenediamine → HCID 178464061, compound

HRID 364293Notes

Reaction equation

HRID 364293 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-59144447c1c84fb9b60d4f4be80c8e04
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

Loading…