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

HRID 225271

Reaction equation

HRID 225271 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9].CN(C)[CH:13]=[CH:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)=O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH3:24][O:23][C:19]1[CH:18]=[C:17]([C:15]2[N:4]3[CH:5]=[N:6][C:7]([C:8]([NH2:10])=[O:9])=[C:3]3[N:2]=[CH:13][CH:14]=2)[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 517045Sodium AcetateHCID 425737963-Dimethylamino-3'-methoxyacrylophenone

Product 1

HCID 146774744-(m-Methoxyphenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.62 g. of 4-amino-5-imidazolecaboxamide hydrochloride, 3-dimethylamino-3'-methoxyacrylophenone, 0.82 g. of sodium acetate and 25 ml. of glacial acetic acid is refluxed for 10 hours. The mixture is evaporated to dryness and the residue worked up to give 4-(m-methoxyphenyl)imidazo[1,5-a]pyrimidine-8-carboxamide. This compound is treated as for Example 29 with trifluoroacetic anhydride to give the product of the example.

Workup

  1. additionA mixture of 1.62 g
  2. customThe mixture is evaporated to dryness

Sources & evidence

ORD record
ord-12c217d117a749b1a77ed7237de14d30
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Linked notes

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