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

HRID 1804550Notes

Reaction equation

HRID 1804550 reaction equation
NCCC1N=CNC=1.[C:9]([N:16]1[CH:20]=[CH:19]N=C1)([N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)=[O:10]>CN(C)C=O>[CH:14]1[N:13]=[CH:12][N:11]2[C:15]=1[CH2:19][CH2:20][NH:16][C:9]2=[O:10]

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
70 °C

Procedure

50.00 g (450 mmol) histamine are dissolved in 1500 ml dimethylformamide, 73.87 g (450 mmol) carbonyldiimidazole are added. The reaction mixture is stirred for 5 hours at 70° C. and for 16 hours at ambient temperature. Then it is evaporated down, and the residue is extracted hot from acetonitrile.

Workup

  1. customThen it is evaporated down
  2. extractionthe residue is extracted hot from acetonitrile

Sources & evidence

ORD record
ord-1f77fd769f154b448e92726d1d24c1b2
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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