Hydrogen Peroxide → 7-[4-(1-Amino-cyclobutyl)-phenyl]-6-phenyl-imidazo[1,2-a]pyrimidine-3-carboxylic Acid Amide

HRID 2362165Notes

Reaction equation

HRID 2362165 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:16][N:15]4[C:24]([C:27]#[N:28])=[CH:25][N:26]=[C:14]4[N:13]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.[OH:29]O>CS(C)=O.CC(=O)OCC>[NH2:1][C:2]1([C:6]2[CH:7]=[CH:8][C:9]([C:12]3[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:16][N:15]4[C:24]([C:27]([NH2:28])=[O:29])=[CH:25][N:26]=[C:14]4[N:13]=3)=[CH:10][CH:11]=2)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 469271627-[4-(1-Amino-cyclobutyl)-phenyl]-6-phenyl-imidazo[1,2-a]pyrimidine-3-carbonitrile

Product 1

HCID 469271637-[4-(1-Amino-cyclobutyl)-phenyl]-6-phenyl-imidazo[1,2-a]pyrimidine-3-carboxylic Acid Amide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of compound 4-10 (40 mg 0.11 mmol.) and K2 CO3 (30 mg, 0.22 mmol) in DMSO (1.0 mL) was added 0.1 mL of H2O2(30% aq.) and the mixture was heated at 60° C. for 3 h. After cooling, the mixture was diluted with 20 mL of EA, the combined organic phase was washed with sat.NaHSO3 (aq) and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.HPLC to give 19 mg of 4-11.

Workup

  1. temperatureAfter cooling
  2. washthe combined organic phase was washed
  3. dry with materialNaHSO3 (aq) and brine, dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by prep.HPLC

Sources & evidence

ORD record
ord-fa79ef82a6514ce785de077cf6585e0a
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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