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

HRID 1199945Notes

Reaction equation

HRID 1199945 reaction equation
C[N:2]([CH3:15])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)=O.Cl.NC1[N:19]=[CH:20][NH:21][C:22]=1[C:23]([NH2:25])=[O:24].C(#N)C.C(O)C>C(O)(=O)C>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([C:5]2[N:19]3[CH:20]=[N:21][C:22]([C:23]([NH2:25])=[O:24])=[C:15]3[N:2]=[CH:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6342AcetonitrileHCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 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 stirred mixture of 15.0 g of 3-dimethylamino-3'-methoxyacrylophenone (prepared as described in Example 5and 9.2 g of 4-amino-5-imidazolecarboxamide hydrochloride in 150 ml of glacial acetic acid was heated at reflux for 24 hours. The solvent was evaporated in vacuo and the crystalline residue was treated with 100 ml of saturated sodium bicarbonate solution, filtered and washed with 200 ml of water to give yellow crystals. This material was treated with 400 ml of acetonitrile then with 600 ml of hot ethanol to give 9.9 g of the product of the example as yellow crystals, mp 249°-252° C.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for 24 hours
  4. customThe solvent was evaporated in vacuo
  5. additionthe crystalline residue was treated with 100 ml of saturated sodium bicarbonate solution
  6. filtrationfiltered
  7. washwashed with 200 ml of water
  8. customto give yellow crystals

Sources & evidence

ORD record
ord-a6850ac1cdbb445c80f6bd9a11cd74eb
Source dataset
uspto-grants-1990_02
Patent number
US04904658

Reaction notes

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