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

HRID 1199951Notes

Reaction equation

HRID 1199951 reaction equation
C[N:2]([CH3:14])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)=O.Cl.NC1[N:18]=[CH:19][NH:20][C:21]=1[C:22]([NH2:24])=[O:23].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:18]3[CH:19]=[N:20][C:21]([C:22]([NH2:24])=[O:23])=[C:14]3[N:2]=[CH:3][CH:4]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 516892Sodium BicarbonateHCID 7300342-Propen-1-one, 3-(dimethylamino)-1-(4-methylphenyl)-

Product 1

HCID 146774804-(4-Methylphenyl)imidazo[1,5-a]pyrimidine-8-carboxamideYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 15.0 g of 3-dimethylamino-4'-methylacrylophenone (prepared as described in Example 11) and 10.0 g of 4-amino-5-imidazolecarboxamide hydrochloride in 150 ml of glacial acetic acid was stirred and heated at reflux for 4 hours. The mixture was evaporated in vacuo to give a yellow crystalline solid. The solid was treated with saturated sodium bicarbonate solution and was collected by filtration, and then it was recrystallized from acetonitrile to give 10.7 g of the desired product as yellow crystals, mp 263°-266° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. customThe mixture was evaporated in vacuo
  4. customto give a yellow crystalline solid
  5. filtrationwas collected by filtration
  6. customit was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-49e3ec8919d94bd5b805e8594b3825f1
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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