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

HRID 1447869Notes

Reaction equation

HRID 1447869 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]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)=O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[F:24][C:23]([F:25])([F:26])[C:19]1[CH:20]=[CH:21][CH:22]=[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:18]=1

Participants

5

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 517045Sodium AcetateHCID 7300243-Dimethylamino-3'-trifluoromethylacrylophenone

Product 1

HCID 146774714-(alpha,alpha,alpha-Trifluoro-m-tolyl)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-imidazolecarboxamide hydrochloride, 2.43 g. of 3-dimethylamino-3'-trifluoromethylacrylophenone and 0.82 g. of sodium acetate in 25 ml. of glacial acetic acid is refluxed for 15 hours and then evaporated to dryness. The residue is treated as described in Example 1, giving the desired product, m.p. 239°-240° C.

Workup

  1. additionA mixture of 1.62 g
  2. customevaporated to dryness
  3. additionThe residue is treated

Sources & evidence

ORD record
ord-a59d3a98cd8c40c596995e8aab32eba2
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Reaction notes

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