1,1'-Carbonyldiimidazole → HCID 11748449, compound

HRID 377501Notes

Reaction equation

HRID 377501 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)[C:9]([NH2:17])=[C:8]([CH:18]([CH3:20])[CH3:19])[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22]>ClC1C=CC=CC=1Cl>[N:1]1([C:6]2[N:7]=[C:8]([CH:18]([CH3:20])[CH3:19])[C:9]3[NH:17][C:21](=[O:22])[C:13]4=[N:14][CH:15]=[CH:16][N:12]4[C:10]=3[N:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 10967548HCID 10967548, compound

Product 1

HCID 11748449HCID 11748449, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Combine 2,4-bis(1H-imidazol-1-yl)-6-(2-propyl)pyrimidin-5-amine (6 g, 22.3 mmol) with 4.5 g (27.8 mmol) of carbonyldiimidazole in 150 mL of 1,2-dichlorobenzene and heat at reflux under N2 for 2 hours. Cool to ambient temperature. Filter the precipitate and wash with CH2Cl2. Dissolve the solids in 500 mL of 10% HCl, treat with charcoal, filter, and make the filtrate basic with NH4OH. Filter the resulting precipitate, wash with water and then with acetone to provide 2-(1H-imidazol-1-yl)-4-(2-propyl)imidazo[2,1-h]pteridin-6(5H)-one; NMR (DMSO+CF3CO2D): δ1.32 (d, 6), 3.84 (m, 1), 7.15 (s, 1), 7.67 (s, 1), 8.04 (s, 1), 8.5 (s, 1) and 8.69 (s, 1 ) ppm.

Workup

  1. temperatureat reflux under N2 for 2 hours
  2. filtrationFilter the precipitate
  3. washwash with CH2Cl2
  4. dissolutionDissolve the solids in 500 mL of 10% HCl
  5. additiontreat with charcoal
  6. filtrationfilter
  7. filtrationFilter the resulting precipitate
  8. washwash with water

Sources & evidence

ORD record
ord-8f4ce73fd89248abb52ca5bf456a27b8
Source dataset
uspto-grants-2000_02
Patent number
US06025489

Reaction notes

Loading…