Hydrochloric Acid → 2-(1H-Imidazol-2-yl)-pyrimidine hydrochloride

HRID 895538Notes

Reaction equation

HRID 895538 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].CO[CH:11](OC)[CH2:12][NH2:13].[ClH:16]>CO>[ClH:16].[NH:2]1[CH:11]=[CH:12][N:13]=[C:1]1[C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 89728Aminoacetaldehyde dimethyl acetalHCID 27579792-Cyanopyrimidine

Product 1

HCID 222603902-(1H-Imidazol-2-yl)-pyrimidine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-Cyanopyrimidine (8.0 g, 76 mmol, prepared according to Liebigs Ann.Chem. 2, 1981, 333-341) and Aminoacetaldehyde dimethyl acetal (8 g, 76 mmol) is heated at 100° C. for 4 hours, cooled, and 100 mL of MeOH and 5 mL of concentrated HCl are added. The mixture is heated at reflux with stirring for 30 hours, cooled and evaporated to dryness in vacuo. 50 mL of i-PrOH is added to the residue and the mixture is heated at reflux with stirring for 30 minutes and cooled. The crystals are collected by filtration, washed with ether, and dried to give the title compound. 1H NMR (DMSO): δ 9.08 (d, 2H), 7.87 (s, 2H), 7.75 (t, 1H). LRMS calcd 146, found 147 (MH+).

Workup

  1. temperaturecooled
  2. temperatureThe mixture is heated
  3. temperatureat reflux
  4. temperaturecooled
  5. customevaporated to dryness in vacuo
  6. addition50 mL of i-PrOH is added to the residue
  7. temperaturethe mixture is heated
  8. temperatureat reflux
  9. stirringwith stirring for 30 minutes
  10. temperaturecooled
  11. filtrationThe crystals are collected by filtration
  12. washwashed with ether
  13. customdried

Sources & evidence

ORD record
ord-cd5290fedf444f9db833d18e27e7b035
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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