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

HRID 241455

반응식

HRID 241455 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-56429fc81c1e4b6f8d53c99e3a7d1987
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648200B2

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