2-Aminopyrimidine → 2-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

HRID 241455

Reaction equation

HRID 241455 reaction equation
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=O.[NH2:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1>CCO>[CH3:15][C:2]1[N:16]=[C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]2[C:3]=1[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 104238192-Bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one

Product 1

HCID 710597752-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidineYield 46.85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 2-bromo-1-[4-(trifluoromethyl)phenyl]propan-1-one (7.120 g, 25.332 mmol), and 2-aminopyrimidine (5.464 g, 55.729 mmol) in EtOH (40 mL). Heat the mixture to reflux, and stir for 24 hours. Cool to room temperature, and concentrate under reduced pressure. Dissolve the residue in EtOAc (750 mL). Sequentially wash the organic extracts with a saturated NaS2O3 aqueous solution (250 mL), a saturated NaHCO3 aqueous solution (250 mL), and a saturated NaCl aqueous solution (350 mL). Crystallize the orange residue from heptanes/EtOAc. Collect the title compound as a white solid (3.290 g, 46.85% yield). 1H NMR (399.83 MHz, d6-DMSO) δ 8.84 (dd, J=1.9, 7.0 Hz, 1H), 8.54 (dd, J=2.0, 4.2 Hz, 1H), 8.06-8.04 (m, 2H), 7.83-7.81 (m, 2H), 7.10 (dd, J=4.1, 6.9 Hz, 1H), 2.68 (s, 3H). ES/MS (m/z) 277.99.

Workup

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. concentrationconcentrate under reduced pressure
  4. dissolutionDissolve the residue in EtOAc (750 mL)
  5. washSequentially wash the organic extracts with a saturated NaS2O3 aqueous solution (250 mL)
  6. customCrystallize the orange residue from heptanes/EtOAc

Sources & evidence

ORD record
ord-56429fc81c1e4b6f8d53c99e3a7d1987
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Linked notes

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