p-Toluenesulfonic acid → HCID 178499054, compound

HRID 536135Notes

Reaction equation

HRID 536135 reaction equation
C(O/[C:5](/[C:15]([O:17][CH3:18])=[O:16])=[C:6](/[O:11]C(=O)C)\[C:7]([O:9]C)=O)(=O)C.[NH2:19][C:20]1[NH:21][CH:22]=[CH:23][N:24]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>CO>[CH3:18][O:17][C:15]([C:5]1[N:19]=[C:20]2[NH:24][CH:23]=[CH:22][N:21]2[C:7](=[O:9])[C:6]=1[OH:11])=[O:16]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 821402-AminoimidazoleHCID 13100501HCID 13100501, compound

Product 1

HCID 178499054HCID 178499054, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl diacetoxyfumarate (3.2 g, 12 mmol), 2-amino imidazole (1.03 g, 12 mmol) and p-toluenesulphonic acid (395 mg, 2.0 mmol were mixed in a 25 mL flask and immersed in a preheated oil bath (120° C.). After 6 h, the reaction mixture was cooled to room temperature and ethyl acetate (10 mL) and methanol (0.6 mL) were added to the residue and the mixture was sonicated for 2 min. The resulting precipitate was collected by filtration, washed with cold ethyl acetate (1 mL) and dried on the pump to give crude product. Recrystallization from methanol gave 6-hydroxy-5-oxo-1,5-dihydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid methyl ester (1.03 g, 41%).

Workup

  1. customimmersed in a preheated oil bath
  2. custom(120° C.)
  3. customthe mixture was sonicated for 2 min
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with cold ethyl acetate (1 mL)
  6. customdried on the pump
  7. customto give crude product
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-40d8c067182446a48760fbaf4737a455
Source dataset
uspto-grants-2014_10
Patent number
US08859563B2

Reaction notes

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