Imidazole → HCID 135815252, compound

HRID 1977638Notes

Reaction equation

HRID 1977638 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[NH:8][C:9](=[O:20])[C:10]3[N:15]([CH3:16])[N:14]=[C:13]([CH2:17][CH2:18][CH3:19])[C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.C(=O)([O-])[O-].[K+].[K+].II>CN1CCCC1=O.[Cu]>[N:23]1([C:2]2[CH:22]=[CH:21][C:5]([CH2:6][C:7]3[NH:8][C:9](=[O:20])[C:10]4[N:15]([CH3:16])[N:14]=[C:13]([CH2:17][CH2:18][CH3:19])[C:11]=4[N:12]=3)=[CH:4][CH:3]=2)[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11430Potassium CarbonateHCID 135815249HCID 135815249, compound

Product 1

HCID 135815252HCID 135815252, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-(4-Bromobenzyl)-1-methyl-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-7-one (390 mg, 0.00108 mol), imidazole (380 mg, 0.00558 mol), potassium carbonate (160 mg, 0.00116 mol), copper bronze (75 mg) and iodine (46 mg, 0.00018 mol) in N-methyl-2-pyrrolidinone (6 ml) were heated under a nitrogen atmosphere at 200° C. for 3 hours. On cooling, the mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate (10 ml) and water (10 ml). The aqueous phase was extracted with ethyl acetate (30 ml), and the combined organic extracts washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure.

Workup

  1. temperatureOn cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue partitioned between ethyl acetate (10 ml) and water (10 ml)
  4. extractionThe aqueous phase was extracted with ethyl acetate (30 ml)
  5. washthe combined organic extracts washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70a7ef0ebacc4ced9e7a9006efbd7fdf
Source dataset
uspto-grants-2001_05
Patent number
US06235742B1

Reaction notes

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