5-Aminoimidazole-4-carboxamide hydrochloride → 4-Phenylimidazo[1,5-a]pyrimidine-8-carboxamide

HRID 1199944Notes

Reaction equation

HRID 1199944 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]=[CH:19][CH:18]=1)=O.C(=O)(O)[O-].[Na+]>C(O)(=O)C.ClCCl>[C:17]1([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]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 146774704-Phenylimidazo[1,5-a]pyrimidine-8-carboxamideYield 43.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 11.0 g of 4-amino-5-imidazolecarboxamide hydrochloride and 15.0 g of 3-dimethylaminoacrylophenone (prepared as described in Example 1) in 120 ml of glacial acetic acid was heated at reflux for 4 hours. The solvent was evaporated in vacuo to give a dark oil which was dissolved in dichloromethane, then treated by stirring with saturated sodium bicarbonate. The organic solvent was evaporated and the remaining mixture was filtered and the solid was washed with water, dried, and then was recrystallized from ethanol to give 7.08 g of the desired product as a yellow solid, mp 226°-228° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was evaporated in vacuo
  4. customto give a dark oil which
  5. additiontreated
  6. customThe organic solvent was evaporated
  7. filtrationthe remaining mixture was filtered
  8. washthe solid was washed with water
  9. customdried
  10. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-0a337bbbb45748e3ae6698465a97ef70
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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