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

HRID 1014960Notes

Reaction equation

HRID 1014960 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].Cl.Cl.CN1C=C(CCN)N=C1.N1C=CN=C1>ClCCl>[CH:6]1[N:5]=[CH:4][N:3]2[C:7]=1[CH2:11][CH2:12][NH:8][C:1]2=[O:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 119576011-Methylhistamine dihydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

Carbonyldiimidazole (970.2 g) was added to a stirred suspension of [2-(1-methyl-1H-imidazol-4-yl)ethyl]amine dihydrochloride (999.9 g) (commercial eg Sigma) and imidazole (37 g) in dichloromethane (5.3 litres) at ca 22° C. The resulting white suspension was heated at reflux until reaction was complete by nmr (4 h.). Solvent (8 litres) was distilled off at atmospheric pressure whilst adding IMS-G (8 litres). Additional IMS-G (2 litres) was added and the suspension cooled to ca. 22° C. and aged at this temperature for at 2 h. The solid was collected by filtration, washed with IMS-G (2×0.5 litres), pulled dry and dried in vacuo at ca. 60° C. to yield the title compound, 478 g.

Workup

  1. temperatureThe resulting white suspension was heated
  2. temperatureat reflux until reaction
  3. customwas complete by nmr (4 h.)
  4. distillationSolvent (8 litres) was distilled off at atmospheric pressure
  5. additionwhilst adding IMS-G (8 litres)
  6. additionAdditional IMS-G (2 litres) was added
  7. customaged at this temperature for at 2 h
  8. filtrationThe solid was collected by filtration
  9. washwashed with IMS-G (2×0.5 litres)
  10. custompulled dry
  11. customdried in vacuo at ca. 60° C.

Sources & evidence

ORD record
ord-f59b030ceb5546eba37cbfdab557ad52
Source dataset
uspto-grants-2011_07
Patent number
US07985740B2

Reaction notes

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