5-Aminoimidazole-4-carboxamide hydrochloride → 4-(3-Chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

HRID 477449Notes

Reaction equation

HRID 477449 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9].[Cl:11][C:12]1[CH:13]=[C:14]([C:18](=O)[CH:19]=[CH:20]N(C)C)[CH:15]=[CH:16][CH:17]=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([C:18]2[N:4]3[CH:5]=[N:6][C:7]([C:8]([NH2:10])=[O:9])=[C:3]3[N:2]=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 516892Sodium BicarbonateHCID 7300651-(3-Chlorophenyl)-3-(dimethylamino)-2-propen-1-one

Product 1

HCID 146774724-(3-Chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamideYield 43.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 13.9 g of 4-amino-5-imidazolecarboxamide hydrochloride, 24.0 g of 3'-chloro-3-dimethylaminoacrylophenone (U.S. Pat. No. 4,209,621, Ex. 50) and 200 ml glacial acetic acid was heated at reflux for 5 hours. The liquid was evaporated in vacuo to give a yellow solid. The excess acid was neutralized with saturated sodium bicarbonate solution and this mixture was filtered and the solid was washed with water and then was dried. Recrystallization from ethanol-methanol gave 10.2 g of the desired product as yellow crystals, mp 252°-254° C.

Workup

  1. temperatureat reflux for 5 hours
  2. customThe liquid was evaporated in vacuo
  3. customto give a yellow solid
  4. filtrationthis mixture was filtered
  5. washthe solid was washed with water
  6. customwas dried
  7. customRecrystallization from ethanol-methanol

Sources & evidence

ORD record
ord-11a9915afc3e4933b7253de51e46a817
Source dataset
uspto-grants-1989_12
Patent number
US04888345

Reaction notes

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