Triethylamine → HCID 20208711, compound

HRID 542485Notes

Reaction equation

HRID 542485 reaction equation
Cl.[C:2]1(=[O:20])[N:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([NH2:14])=[NH:13])[C:5](=[O:15])[C:4]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:3]12.C(N(CC)CC)C.Cl[C:29](=[CH2:32])[C:30]#[N:31]>CCO>[NH2:31][C:30]1[CH:29]=[CH:32][N:14]=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]2[C:5](=[O:15])[C:4]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:3]3[C:2]2=[O:20])[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 20208678HCID 20208678, compound

Product 1

HCID 20208711HCID 20208711, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-phthalimidohexanamidine hydrochloride (71.1 g.), triethylamine (170 ml.) and 2-chloroacrylonitrile (57.4 ml.) in EtOH (500 ml.) was heated under reflux for 2 hours. The solvent was evaporated and the residue was partitioned between EtOAc and 2N aqueous HCl. The aqueous layer was basified with 10N aqueous NaOH and the product was extracted with EtOAc, dried (MgSO4) and evaporated to dryness. The residual gum was dissolved in EtOAc and treated with excess of a solution of maleic acid in EtOAc. The precipitated solid was dissolved in water, basified with 10N aqueous sodium hydroxide, extracted with EtOAc, the extract dried (MgSO4) and evaporated. The residual solid was triturated with acetonitrile to give 4-amino-2-(5-phthalimidopentyl)pyrimidine as a brown solid (37.9 g.), m.p. 101°-4°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between EtOAc and 2N aqueous HCl
  5. extractionthe product was extracted with EtOAc
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. dissolutionThe residual gum was dissolved in EtOAc
  9. additiontreated with excess of a solution of maleic acid in EtOAc
  10. dissolutionThe precipitated solid was dissolved in water
  11. extractionextracted with EtOAc
  12. dry with materialthe extract dried (MgSO4)
  13. customevaporated
  14. customThe residual solid was triturated with acetonitrile

Sources & evidence

ORD record
ord-361f7b281cef476283c0e9b7ca2178e1
Source dataset
uspto-grants-1987_04
Patent number
US04657908

Reaction notes

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