Ammonia → HCID 53678275, compound

HRID 542487Notes

Reaction equation

HRID 542487 reaction equation
[CH2:1]([NH:4][C:5](=S)[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]2C(=O)C3=CC=CC=C3C2=O)[N:8]=1)[CH2:2][CH3:3].[NH3:30]>CN(C=O)C>[CH2:1]([N:4]=[C:5]([NH2:30])[NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[N:8]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53767345HCID 53767345, compound

Product 1

HCID 53678275HCID 53678275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-propylthioureido)-2-(5-phthalimidopentyl)pyrimidine (1.7 g.), DMF (25 ml.) saturated ethanolic ammonia (10 ml.) and yellow mercuric oxide (1.1 g.) was stirred at room temperature for 2 hours. The mixture was evaporated to dryness and the residue was redissolved in ethanol, filtered and the filtrate evaporated to dryness. A solution of this residue in EtOH (20 ml.) was treated with hydrazine (5 ml.) and stirred at room temperature for 16 hours. The mixture was evaporated to dryness and the residue was dissolved in water, acidified with 2N aqueous HCl and filtered. The filtrate was basified with 10N aqueous NaOH and the mixture was extracted twice with EtOAc. The extract was dried (MgSO4) and evaporated to give 4-[2-propylguanidino]-2-(5-aminopentyl)pyrimidine as a gum (0.4 g.) which was used without further purification.

Workup

  1. customThe mixture was evaporated to dryness
  2. dissolutionthe residue was redissolved in ethanol
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness
  5. additionA solution of this residue in EtOH (20 ml.) was treated with hydrazine (5 ml.)
  6. stirringstirred at room temperature for 16 hours
  7. customThe mixture was evaporated to dryness
  8. dissolutionthe residue was dissolved in water
  9. filtrationfiltered
  10. extractionthe mixture was extracted twice with EtOAc
  11. dry with materialThe extract was dried (MgSO4)
  12. customevaporated

Sources & evidence

ORD record
ord-cffdaa9156c547b682c16460c9ac735c
Source dataset
uspto-grants-1987_04
Patent number
US04657908

Reaction notes

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