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

HRID 2110920Notes

Reaction equation

HRID 2110920 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 the mixture is evaporated down, the residue is extracted hot from acetonitrile.

Workup

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

Sources & evidence

ORD record
ord-c76658a52eb140d9937e003fbf09d38e
Source dataset
uspto-grants-2009_04
Patent number
US07517995B2

Reaction notes

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