Phenacyl bromide → {1-[4-(2,6-Diphenyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

HRID 2362167Notes

Reaction equation

HRID 2362167 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]=[C:20]([NH2:30])[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:33][C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=O>C(O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][N:21]4[CH:33]=[C:34]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[N:30]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 66823192{1-[4-(2-Amino-5-phenyl-pyrimidin-4-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

Product 1

HCID 66823455{1-[4-(2,6-Diphenyl-imidazo[1,2-a]pyrimidin-7-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl EsterYield 48.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-1 (150 mg, 0.36 mmol) and 2-Bromo-1-phenyl-ethanone (110 mg, 0.54 mmol) in ethanol (2 mL) was heated to 100° C. and stirred for 45 mins under microwave radiation. The mixture was cooled to r.t. and diluted with 20 mL of DCM. The organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 90 mg of 5-2.

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by prep.TLC

Sources & evidence

ORD record
ord-a8610434272c41c18af19fb172a6ba43
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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