1,1'-Carbonyldiimidazole → 5H,6H,7H,8H-imidazo(1,5-c)pyrimidin-5-one

HRID 1715254Notes

Reaction equation

HRID 1715254 reaction equation
N1C=C(CCN)N=C1.[CH:9]1[N:13]=[CH:12][N:11]([C:14]([N:16]2C=N[CH:18]=[CH:17]2)=[O:15])[CH:10]=1>CN(C=O)C>[CH:9]1[N:13]=[CH:12][N:11]2[C:10]=1[CH2:18][CH2:17][NH:16][C:14]2=[O:15]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 178419017HCID 178419017, compound

Product 1

HCID 14875185H,6H,7H,8H-imidazo(1,5-c)pyrimidin-5-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(1H-imidazol-4-yl)ethanamine (26.8 g; 240.9 mmol; 1 eq) and CDI (39.1 g; 240.9 mmol; 1 eq) in DMF (401.7 ml) is stirred at 50° C. for two days. The mixture is concentrated to 100 ml and acetonitrile (200 ml) is added. The resulting precipitate is filtered, washed with acetonitrile (2×50 ml) and dried under vacuum, affording the title compound that is used in the next step without further purification (28.3 g; 85%).

Workup

  1. concentrationThe mixture is concentrated to 100 ml and acetonitrile (200 ml)
  2. additionis added
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with acetonitrile (2×50 ml)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ebd9bbfdfe254e7bb00fcb6969a95043
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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