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

HRID 225255

Reaction equation

HRID 225255 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-c4aca6425bf1473183d71155aea10868
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Linked notes

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