Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Diphenyl Ether | HCID 7583 | — |
| Reactant | 2-Aminoimidazole | HCID 82140 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59396059 | HCID 59396059 | — |
Reaction Steps
As shown in Reaction Scheme A, imidazolo[1,2-a]pyrimidone (iva) can be prepared from alpha-bromoheteroaryl ketone (R═alkyl). Thus, cyclization of bromoketone (ia) with acetyl guanidine in an appropriate solvent such as dimethylformamide at a temperature of 25-120° C. for a period of 1-72 hours to give 2-acetamidoimidazole (iia), which can be hydrolyzed with an acid such as sulfuric acid in an appropriate solvent such as water or ethanol at a temperature of 60-120° C. for a period of 2-24 hours to give 2-aminioimidazole (iiia). 2-Aminoimidazole (iiia) can be modified by cyclization with substituted acrylate in an inert solvent such as methanol, dioxane or phenylether at a temperature of 60-260° C. for a period of 0.5-16 hours to give imidazolo[1,2-a]pyrimidone (iva).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06346534B1 |
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| Source dataset | uspto-grants-2002_02 |
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| ORD ID | ord-62c9adf6df09471180ce41029d240fcf |
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| Source note | uspto-grants-2002_02 |
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