5-Aminoimidazole-4-carboxamide hydrochloride → 4-(2-Thienyl)imidazo[1,5-a]pyrimidine-8-carboxamide

HRID 1758794Notes

Reaction equation

HRID 1758794 reaction equation
C[N:2]([CH3:12])[CH:3]=[CH:4][C:5]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)=O.Cl.NC1[N:16]=[CH:17][NH:18][C:19]=1[C:20]([NH2:22])=[O:21].C([O-])(=O)C.[Na+]>C(O)(=O)C>[S:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]1[N:16]2[CH:17]=[N:18][C:19]([C:20]([NH2:22])=[O:21])=[C:12]2[N:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 517045Sodium AcetateHCID 6023993-(Dimethylamino)-1-(2-thienyl)-2-propen-1-one

Product 1

HCID 205089574-(2-Thienyl)imidazo[1,5-a]pyrimidine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.01 mol of 3-dimethylamino-1-(2-thienyl)-2-propen-1-one (prepared as described in Example 1, Part A), 0.01 mol of 4amino-5-imidazolecarboxamide hydrochloride and 0.01 mol of anhydrous sodium acetate in 25 ml. of glacial acetic acid can be refluxed for 16 hours. The reaction mixture can be cooled and the crystalline precipitate collected by filtration and washed with water to produce 4-(2-thienyl)imidazo[1,5-a]pyrimidine-8-carboxamide.

Workup

  1. customprepared
  2. temperatureThe reaction mixture can be cooled
  3. filtrationthe crystalline precipitate collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-aead6c4625aa4cd5aa47356fb23eea00
Source dataset
uspto-grants-1983_02
Patent number
US04374988

Reaction notes

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