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

HRID 241433

반응식

HRID 241433 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 (40.0 mL). Heat the mixture to reflux, and stir for 24 hours. Concentrate in vacuo. Dissolve the residue in EtOAc (750 mL); and wash sequentially with saturated aqueous NaS2O3 (250 mL), saturated aqueous NaHCO3 (250 mL), and saturated NaCl (350 mL). Crystallize the orange residue from heptanes/EtOAc to give the title product as a white solid (3.29 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).

후처리

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. concentrationConcentrate in vacuo
  4. dissolutionDissolve the residue in EtOAc (750 mL)
  5. washand wash sequentially with saturated aqueous NaS2O3 (250 mL), saturated aqueous NaHCO3 (250 mL), and saturated NaCl (350 mL)
  6. customCrystallize the orange residue from heptanes/EtOAc

출처 및 근거

ORD 기록
ord-0e2f83dc904c4fa99ffb89a762c8d4f7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648200B2

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