Pyridine → HCID 59749173, compound

HRID 747175Notes

Reaction equation

HRID 747175 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]2[CH:14]=[CH:15][C:16](=[O:19])[NH:17][CH:18]=2)=[CH:4][N:3]=1.[S:20]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21]1.N1C=CC=CC=1>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]2[CH:14]=[CH:15][C:16](=[O:19])[N:17]([C:22]3[CH:23]=[CH:24][S:20][CH:21]=3)[CH:18]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 581760Thiophene-3-boronic acidHCID 59749106HCID 59749106, compound

Product 1

HCID 59749173HCID 59749173, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

In a reaction vessel, 5-[2-amino-4-(2-furyl)-5-pyrimidinyl]-1,2-dihydro-2-pyridinone (50 mg, 0.197 mmol), thiophene-3-boronic acid (50 mg, 0.393 mmol), and copper acetate (4 mg, 0.0197 mmol) were suspended in N,N-dimethylformamide (3 ml). Pyridine (31 mg, 0.393 mmol) was added thereto, followed by stirring at room temperature for 14.5 hours in the air. After the reaction was terminated, the mixture was concentrated and suspended in dimethylsulfoxide. Subsequently, the insoluble matters were removed by filtration and the resulting filtrate was purified by HPLC, to give the title compound (34 mg, 51%) as a pale yellow solid.

Workup

  1. customAfter the reaction was terminated
  2. concentrationthe mixture was concentrated
  3. customSubsequently, the insoluble matters were removed by filtration
  4. customthe resulting filtrate was purified by HPLC

Sources & evidence

ORD record
ord-e270388ff9c846fea8d493f5703eaf8b
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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