ethyl 4-amino-1H-imidazole-5-carboxylate → Ethyl 4-(2-thienyl)imidazo[1,5-a]pyrimidine-8carboxylate

HRID 1758797

Reaction equation

HRID 1758797 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CN(C)[CH:14]=[CH:15][C:16]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)=O>C(O)(=O)C>[S:19]1[CH:20]=[CH:21][CH:22]=[C:18]1[C:16]1[N:3]2[CH:4]=[N:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]2[N:1]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 343359ethyl 4-amino-1H-imidazole-5-carboxylateHCID 6023993-(Dimethylamino)-1-(2-thienyl)-2-propen-1-one

Product 1

HCID 20508943Ethyl 4-(2-thienyl)imidazo[1,5-a]pyrimidine-8carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.55 g. (0.01 mols) of ethyl 4-amino-5-imidazolecarboxylate and 1.81 g. (0.01 mols) of 3-dimethylamino-1-(2-thienyl)-2-propen-1-one (prepared as described in Example 1, Part A) in 25 ml. of glacial acetic acid can be refluxed for 16 hours, then cooled and evaporated to dryness in vacuo. The residue can be dissolved in dichloromethane and passed through a short column of hydrous magnesium silicate. The effluent can be refluxed on a steam bath with a slow constant addition of n-hexane. At the first appearance of crystallization, heating should be curtailed and the solution allowed to cool. The precipitated material can be collected by filtration to produce ethyl 4-(2-thienyl)imidazo[1,5-a]pyrimidine-8carboxylate.

Workup

  1. additionA mixture of 1.55 g
  2. temperaturecooled
  3. customevaporated to dryness in vacuo
  4. dissolutionThe residue can be dissolved in dichloromethane
  5. temperatureThe effluent can be refluxed on a steam bath with a slow constant addition of n-hexane
  6. customAt the first appearance of crystallization
  7. temperatureheating should
  8. temperatureto cool
  9. filtrationThe precipitated material can be collected by filtration

Sources & evidence

ORD record
ord-32b07c49195d4ad6be6067c3e13a9c5c
Source dataset
uspto-grants-1983_02
Patent number
US04374988

Linked notes

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