Water → HCID 59396059, compound

HRID 1699356Notes

Reaction equation

HRID 1699356 reaction equation
S(=O)(=O)(O)O.[OH2:6].[NH2:7][C:8]1[NH:9][CH:10]=[CH:11][N:12]=1.[C:13]1(OC2C=CC=CC=2)[CH:18]=CC=C[CH:14]=1>O1CCOCC1.CO.C(O)C>[N:9]1[C:10](=[O:6])[CH2:11][N:12]2[CH:14]=[CH:13][CH:18]=[N:7][C:8]=12

Participants

8

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7583Diphenyl EtherHCID 821402-Aminoimidazole

Product 1

HCID 59396059HCID 59396059, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  1. customto give 2-aminioimidazole (iiia)

Sources & evidence

ORD record
ord-62c9adf6df09471180ce41029d240fcf
Source dataset
uspto-grants-2002_02
Patent number
US06346534B1

Reaction notes

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