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

HRID 1199946Notes

Reaction equation

HRID 1199946 reaction equation
C[N:2]([CH3:17])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)=O.Cl.NC1[N:21]=[CH:22][NH:23][C:24]=1[C:25]([NH2:27])=[O:26].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:16][O:15][C:9]1[CH:8]=[C:7]([C:5]2[N:21]3[CH:22]=[N:23][C:24]([C:25]([NH2:27])=[O:26])=[C:17]3[N:2]=[CH:3][CH:4]=2)[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 516892Sodium BicarbonateHCID 1481361(E)-1-(3,4-dimethoxyphenyl)-3-(dimethylamino)-2-propen-1-one

Product 1

HCID 146774754-(3,4-Dimethoxyphenyl)imidazo[1,5-a]pyrimidine-8-carboxamideYield 53.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 15.0 g of 3-dimethylamino-3',4'-dimethoxyacrylophenone (prepared as described in Example 6) and 8.0 g of 4-amino-5-imidazolecarboxamide hydrochloride in 150 ml of glacial acetic acid was heated at reflux for 24 hours. The solvent was evaporated in vacuo to give an oil. The oil solidified on standing at room temperature. The solid was treated with 200 ml of saturated sodium bicarbonate solution and then filtered to collect the crystals. The material was treated by boiling with 700 ml of ethanol and then was filtered. The solid was recrystallized from methanol-chloroform to give 7.9 g of the desired product, mp 262°-265° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was evaporated in vacuo
  4. customto give an oil
  5. customon standing at room temperature
  6. filtrationfiltered
  7. customto collect the crystals
  8. additionThe material was treated
  9. filtrationwas filtered
  10. customThe solid was recrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-64ed4a5eceae4ba185a46e65de2291fa
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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