Imidazole → HCID 68974947, compound

HRID 658272Notes

Reaction equation

HRID 658272 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:4](=[O:14])[N:3]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.C1C[O:23]CC1>C(Cl)Cl>[NH2:17][CH2:18][CH2:19][NH:15][C:16]([NH:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:4](=[O:14])[N:3]=1)=[O:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8028TetrahydrofuranHCID 68973119HCID 68973119, compound

Product 1

HCID 68974947HCID 68974947, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-1-hexyl-1H-pyrimidin-2-one (C) (0.10 g, 0.513 mmol) in dry CH2Cl2 (7 ml) was added N,N carbonyl diimidazole (0.131 g, 0.513 mmol) and the solution was stirred at room temperature for 16 h. The solvent was evaporated and the residue redissolved in dry chloroform Hexane was then added to precipitate the intermediate, which was dried in vacuo and used directly without further purification. To a solution of the resulting imidazole intermediate (0.100 g, 0.346 mmol) was added to a solution of ethyldiamine (0.14 ml, 2.07 mmol) in dry THF (5 ml). The solution was stirred at room temperature for 16 h under N2 atmosphere. The solvents were then evaporated and the residue was dissolved in chloroform and washed with water and brine. The organic phases were combined and dried over MgSO4. The solvent was evaporated in vacuo and the crude compound was purified through flash silica gel chromatography (CHCl3/MeOH/Et3N (1:2:0.1)) to afford pure compound (L) (0.080 g, 82%)

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue redissolved in dry chloroform Hexane
  3. additionwas then added
  4. customto precipitate the intermediate, which
  5. customwas dried in vacuo
  6. customused directly without further purification
  7. stirringThe solution was stirred at room temperature for 16 h under N2 atmosphere
  8. customThe solvents were then evaporated
  9. dissolutionthe residue was dissolved in chloroform
  10. washwashed with water and brine
  11. dry with materialdried over MgSO4
  12. customThe solvent was evaporated in vacuo
  13. customthe crude compound was purified through flash silica gel chromatography (CHCl3/MeOH/Et3N (1:2:0.1))

Sources & evidence

ORD record
ord-0f13864c1b1a41c2a22a0bd3d6173236
Source dataset
uspto-grants-2011_12
Patent number
US08076426B2

Reaction notes

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