5-Aminoimidazole-4-carboxamide hydrochloride → 4-(3,4-Dichlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

HRID 1199949

Reaction equation

HRID 1199949 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH:10]=[CH:11][N:12]([CH3:14])C)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.NC1[N:19]=[CH:20][NH:21][C:22]=1[C:23]([NH2:25])=[O:24]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:19]3[CH:20]=[N:21][C:22]([C:23]([NH2:25])=[O:24])=[C:14]3[N:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 28051561-(3,4-Dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one

Product 1

HCID 146774784-(3,4-Dichlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamideYield 49.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 12.0 g of 3',4'-dichloro-3-dimethylaminoacrylophenone (prepared as described in Example 9) and 6.3 g of 4-amino-5-imidazolecarboxamide hydrochloride in 450 ml of glacial acetic acid was heated at reflux for 24 hours. The reaction mixture was allowed to stand at room temperature for 16 hours then the mixture was filtered and the crystals that were collected were washed with 300 ml of saturated sodium bicarbonate and then were washed with water. This material was dried, washed with hot methanol and filtered to give 5.9 g of the desired product as yellow crystals, mp 302°-304° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. filtrationthe mixture was filtered
  4. customthe crystals that were collected
  5. washwere washed with 300 ml of saturated sodium bicarbonate
  6. washwere washed with water
  7. customThis material was dried
  8. washwashed with hot methanol
  9. filtrationfiltered

Sources & evidence

ORD record
ord-0cddb427d58148fa98f48d757f72a635
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Linked notes

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